GB478525A - Process for the preparation of diphenylguanidine - Google Patents

Process for the preparation of diphenylguanidine

Info

Publication number
GB478525A
GB478525A GB22492/36A GB2249236A GB478525A GB 478525 A GB478525 A GB 478525A GB 22492/36 A GB22492/36 A GB 22492/36A GB 2249236 A GB2249236 A GB 2249236A GB 478525 A GB478525 A GB 478525A
Authority
GB
United Kingdom
Prior art keywords
cyanogen chloride
pipe
anhydrous
passing
chloride
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB22492/36A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of GB478525A publication Critical patent/GB478525A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Diphenylguanidine hydrochloride is produced by the action of a slight excess of anhydrous cyanogen chloride, prepared as described below, on anhydrous aniline, preferably in counterflow. The cyanogen chloride is prepared by passing the stoichiometric amount of chlorine into aqueous sodium cyanide solution at below 15,5 DEG C., then adding sufficient caustic alkali to establish a faintly alkaline reaction, heating the liquid or passing steam therethrough to cause evolution of cyanogen chloride, and passing the latter over calcium chloride or like dehydrating agent, if desired after cooling. As shown, cyanogen chloride is generated in a number of vessels, 1 each provided with heating or cooling jackets and coils 2, 5, a chlorine supply pipe 9, a cyanide solution supply pipe 12, and an outlet pipe 15 for the cyanogen chloride. Pipes (not shown) for admitting caustic alkali solution are also provided. The cyanogen chloride passes by a pipe 17 to a <PICT:0478525/IV/1> cooling coil 18 and a drying tower 21, and thence in turn through a series of reaction vessels 25, 25<1>, 25<11>, through which anhydrous aniline, supplied by a pipe 30, flows in the opposite direction. Fused diphenylguanidine hydrochloride collects in a vessel 34, and is withdrawn through a pipe 35 and converted into diphenylguanidine in known manner. The slight excess of cyanogen chloride is withdrawn through a pipe 29, which is preferably connected to a source of reduced pressure. The cyanogen chloride generators are preferably operated alternately, and may be connected to a gas holder. British Specification 255,220, [Class 2 (iii)], and U.S.A. Specifications 1,884,509 and 1,897,220 are referred to. The Specification as open to inspection under Sect. 91 refers generally to the manufacture of guanidine derivatives by treating an anhydrous amine in counterflow with an anhydrous gaseous cyanogen halide. It states that the amine may be dissolved or dispersed in an anhydrous medium, and mentions methylamine and toluidine as amines which may be treated. This subject-matter does not appear in the Specification as accepted.ALSO:<PICT:0478525/III/1> Cyanogen chloride is prepared by passing the stoichiometric amount of chlorine into aqueous sodium cyanide solution at below 15,5 DEG C., then adding sufficient caustic alkali to establish a faintly alkaline reaction, heating the liquid or passing steam therethrough to cause evolution of cyanogen chloride, and passing the latter over calcium chloride or like dehydrating agent, if desired, after cooling. Apparatus is described comprising a number of vessels 1 each provided with heating or cooling jackets and coils 2, 5, a chlorine supply pipe 9, a cyanide solution supply pipe 12, and an outlet pipe 15 for the cyanogen chloride. Pipes (not shown) for admitting caustic alkali solution are also provided. The cyanogen chloride passes by a pipe 17 to a cooling coil 18 and a drying tower 21, and thence in turn through a series of reaction vessels 25, 25<1>, 25<11> in which it is utilized for the manufacture of diphenyl-guanidine.
GB22492/36A 1936-02-13 1936-08-14 Process for the preparation of diphenylguanidine Expired GB478525A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE478525X 1936-02-13

Publications (1)

Publication Number Publication Date
GB478525A true GB478525A (en) 1938-01-20

Family

ID=6542263

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22492/36A Expired GB478525A (en) 1936-02-13 1936-08-14 Process for the preparation of diphenylguanidine

Country Status (1)

Country Link
GB (1) GB478525A (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2615045A (en) * 1950-10-23 1952-10-21 American Cyanamid Co Preparation of diarylguanidines
US4709094A (en) * 1986-07-10 1987-11-24 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Sigma brain receptor ligands and their use
US5262568A (en) * 1990-03-02 1993-11-16 State Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5312840A (en) * 1986-07-10 1994-05-17 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education Substituted guanidines having high binding to the sigma receptor and the use thereof
US5336689A (en) * 1990-03-02 1994-08-09 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5403861A (en) * 1991-02-08 1995-04-04 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5574070A (en) * 1990-05-25 1996-11-12 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5741661A (en) * 1991-02-08 1998-04-21 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5847006A (en) * 1991-02-08 1998-12-08 Cambridge Neuroscience, Inc. Therapeutic guanidines
US5922772A (en) * 1993-11-23 1999-07-13 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6143791A (en) * 1994-02-03 2000-11-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6147063A (en) * 1993-05-27 2000-11-14 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6174924B1 (en) 1994-02-03 2001-01-16 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6251948B1 (en) 1990-03-02 2001-06-26 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US6787569B1 (en) 1994-02-03 2004-09-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US7351743B1 (en) 1994-02-03 2008-04-01 Wyeth Therapeutic guanidines

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2615045A (en) * 1950-10-23 1952-10-21 American Cyanamid Co Preparation of diarylguanidines
US4709094A (en) * 1986-07-10 1987-11-24 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Sigma brain receptor ligands and their use
US5312840A (en) * 1986-07-10 1994-05-17 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education Substituted guanidines having high binding to the sigma receptor and the use thereof
US5262568A (en) * 1990-03-02 1993-11-16 State Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5336689A (en) * 1990-03-02 1994-08-09 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US6251948B1 (en) 1990-03-02 2001-06-26 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5559154A (en) * 1990-03-02 1996-09-24 Oregon State Board Of Higher Education Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5798390A (en) * 1990-03-02 1998-08-25 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5767162A (en) * 1990-03-02 1998-06-16 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5637622A (en) * 1990-03-02 1997-06-10 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5574070A (en) * 1990-05-25 1996-11-12 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5686495A (en) * 1991-02-08 1997-11-11 Cambridge Neuroscience, Inc. Substituted hydrazinedicarboximidamides and methods of use thereof
US6071969A (en) * 1991-02-08 2000-06-06 Cambridge Neuroscience, Inc. Substituted aminoguanidines and methods of use thereof
US5670519A (en) * 1991-02-08 1997-09-23 Cambridge Neuroscience, Inc. Acenaphthyl-substituted guanidines and methods of use thereof
US5672608A (en) * 1991-02-08 1997-09-30 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5677348A (en) * 1991-02-08 1997-10-14 Cambridge Neuroscience, Inc. Substituted aminoguanidines and methods of use thereof
US5637623A (en) * 1991-02-08 1997-06-10 Cambridge Neuroscience, Inc. Substituted adamantyl guanidines and methods of use there of
US5741661A (en) * 1991-02-08 1998-04-21 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5622968A (en) * 1991-02-08 1997-04-22 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5614630A (en) * 1991-02-08 1997-03-25 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5837737A (en) * 1991-02-08 1998-11-17 Cambridge Neuroscience, Inc. Hydrazinedicarboximidamide compounds and pharmaceutical composition comprising same
US5847006A (en) * 1991-02-08 1998-12-08 Cambridge Neuroscience, Inc. Therapeutic guanidines
US5403861A (en) * 1991-02-08 1995-04-04 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5652269A (en) * 1991-02-08 1997-07-29 Cambridge Neuroscience, Inc. Substituted hydrazinecarboximidamides and methods of use thereof
US6147063A (en) * 1993-05-27 2000-11-14 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6153604A (en) * 1993-05-27 2000-11-28 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6013675A (en) * 1993-11-23 2000-01-11 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US5955507A (en) * 1993-11-23 1999-09-21 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6156741A (en) * 1993-11-23 2000-12-05 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US5922772A (en) * 1993-11-23 1999-07-13 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6143791A (en) * 1994-02-03 2000-11-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6174924B1 (en) 1994-02-03 2001-01-16 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6288123B1 (en) 1994-02-03 2001-09-11 Cambridge Neurosciences, Inc. Therapeutic guanidines
US6787569B1 (en) 1994-02-03 2004-09-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US7351743B1 (en) 1994-02-03 2008-04-01 Wyeth Therapeutic guanidines

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