GB800869A - Substituted amino-guanidines - Google Patents

Substituted amino-guanidines

Info

Publication number
GB800869A
GB800869A GB2760355A GB2760355A GB800869A GB 800869 A GB800869 A GB 800869A GB 2760355 A GB2760355 A GB 2760355A GB 2760355 A GB2760355 A GB 2760355A GB 800869 A GB800869 A GB 800869A
Authority
GB
United Kingdom
Prior art keywords
methyl
hydrogen
chlorophenyl
prepared
reacting
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
GB2760355A
Inventor
Stanley Birtwell
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2760355A priority Critical patent/GB800869A/en
Publication of GB800869A publication Critical patent/GB800869A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/16Compounds containing any of the groups, e.g. aminoguanidine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/16Compounds containing any of the groups, e.g. aminoguanidine
    • C07C281/18Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones

Landscapes

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

Abstract

The invention comprises substituted amino-guanidines of the formula: <FORM:0800869/IV (b)/1> and acid addition salts thereof, wherein of A and B one represents phenyl, naphthyl or a tetrahydronaphthyl radical which may be optionally substituted and the other represents hydrogen or an alkyl radical, R, R1 and R11 represent hydrogen or alkyl radicals and R111 represents hydrogen, an alkyl or an aralkyl radical, provided that when B, R, R1, R11 and R111 are hydrogen, A is not phenyl, or p- or o-methoxyphenyl, and when B is methyl and R, R, R11 and R111 are hydrogen then A is not phenyl; and processes for the manufacture thereof by (a) reacting a compound (II) <FORM:0800869/IV (b)/2> or its hydrate or its salts with a compound (III): <FORM:0800869/IV (b)/3> or its salts, preferably in the presence of an inert solvent or diluent; (b) (when B is hydrogen) reacting compound (II) or its salts with a compound: <FORM:0800869/IV (b)/4> preferably in the presence of an inert solvent or diluent; (c) (when R is hydrogen) reacting a compound (II) with a compound: A-N = C = N-B (V) (d) (when R is hydrogen and B is hydrogen or alkyl) reacting a compound: <FORM:0800869/IV (b)/5> with ammonia or an alkylamine; (e) (when R11 is hydrogen) catalytic hydrogenation of a compound <FORM:0800869/IV (b)/6> preferably in the presence of an inert solvent or diluent; wherein X is an alkyl or an aralkyl group, R2 is an alkyl or aryl radical and R3 is hydrogen, an alkyl or an aryl radical. In examples, compounds of the general formula (I), wherein A represents m- and p-chloro- and o-methoxy-phenyl groups, B, R, R1, R11 and R111 being hydrogen, and wherein A represents p-chlorophenyl, R methyl and B, R1, R11 and R111 hydrogen, are prepared by reacting hydrazine monohydrochloride (obtained by mixing hydrazine hydrate and dihydrochloride) with an isothiourea of the general formula (III), wherein A and R represent the groups above and X is a methyl group, in methanol, the products being isolated or converted into the mono- or di-hydrochlorides; compounds wherein A represents 2:4-dimethylphenyl and wherein A represents 2:3-dimethyl phenyl are similarly prepared but using an isothiourea wherein X is, respectively, an ethyl and a benzyl group. In further examples, compound (I) wherein A is 2:4-dichloro-, p-bromo-, p-nitro-, 2-methoxy-5-chloro-, p-iodo, 2:5-dimethyl-, p-n-butyl-, 3-chloro-4-methyl-, 2 - methyl - 4 - chloro -, 3 - methyl - 4 - chloro-, 3:4 - dimethyl -, 2:4:5 - trimethyl -, 2:4 - dichloro - 5 - methyl -, 2 - methoxy - 5 - chloro-, 2 - methyl - 5 - chloro -, p - hydroxy - and 3:4-dichloro-phenyl, a - and b -naphthyl, m- and p-tolyl, diphenylyl, and a - and b -tetrahydronaphthyl, B, R, R1, R11 and R111 being hydrogen; wherein A is phenyl, R methyl and B, R1, R11 and R111 hydrogen; A is p-chlorophenyl, B methyl, and R, R1, R11 and R111 hydrogen; and A is methyl, B phenyl, R methyl and R1, R11 and R111 hydrogen, are prepared by reacting hydrazine hydrate with the hydriodide of an isothiourea (III), wherein A and R represent the groups above and X is a methyl group, in methanol, the product being isolated as the hydriodide or the hydrochloride after treatment with hydrogen chloride. Compounds (I) wherein A is p-chlorophenyl and R11 and R111 methyl; A is p-chlorophenyl and R methyl; and A is p-chlorophenyl and R1 and R111 methyl, the other symbols representing hydrogen, are prepared by reacting a correspondingly substituted cyanamide (IV) with a substituted or unsubstituted hydrazine (II) or its salts, in methanol, the product being isolated as the base or its hydrohalide salt, the base being prepared from the salt by basification. N1-Dimethylamino-N2-p-chlorophenyl - N1:N3 - dimethylguanidine is prepared by reacting an acetone solution of p-chlorophenyl methylcarbodiimide with N1:N1: N2 - trimethylhydrazine; N1 - dimethyl amino-N1 - methyl - N2 - n - butyl - N3 - p - chlorophenylguanidine by reacting N1dimethylamino-N1:S - dimethyl - N2 - p - chlorophenyliso - thiourea hydroidide with n - butylamine, and N1-dimethylamino - N2 - phenylguanidine by reacting N1 - dimethylamino - N2 - phenyl - S-methylisothiourea hydroiodide with ammonia. N1 - benzylamino -, N1 - isopropylamino -, and N1 - nonylamino - N2 - p - chlorophenyl guanidinen hydrochlorides are prepared by catalytic hydrogenation of the corresponding compounds of formula (VII), in methanol, using a platinum catalyst. Starting materials. Isothioureas (III) are prepared by treatment of the corresponding thioureas with a molecular proportion of an alkyl or aralkyl halide, and isolated as the halide salt from which the base may be obtained. The corresponding thioureas are prepared by interaction of the corresponding amine and benzoyl isothiocyanate followed by hydrolysis. N1-p-chlorophenyl - N1:N2:S - trimethylisothiourea is prepared from methyl isothiocyanate and N - methyl - p - chloroaniline to form N1 - p-chlorophenyl - N1:N1 - dimethylthiourea which is treated with methyl iodide. p-Chlorophenylmethyl carbodiimide (acetone solution) is obtained by heating acetone with a small quantity of sulphur, followed by further heating with mercuric oxide and N1-p-chlorophenyl-N2-methyl - thiourea and filtration. N1 - Dimethylamino - N1 - S - dimethyl - N2 - p - chlorophenyl iso thiourea hydroiodide is prepared by reaction of methyl iodide with N1-dimethylamino-N1-methyl - N2 - p - chlorophenylthiourea which is prepared by reacting trimethyl hydrazine with p-chlorophenylisothiocyanate.
GB2760355A 1955-09-28 1955-09-28 Substituted amino-guanidines Expired GB800869A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2760355A GB800869A (en) 1955-09-28 1955-09-28 Substituted amino-guanidines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2760355A GB800869A (en) 1955-09-28 1955-09-28 Substituted amino-guanidines

Publications (1)

Publication Number Publication Date
GB800869A true GB800869A (en) 1958-09-03

Family

ID=10262314

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2760355A Expired GB800869A (en) 1955-09-28 1955-09-28 Substituted amino-guanidines

Country Status (1)

Country Link
GB (1) GB800869A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3344186A (en) * 1964-03-03 1967-09-26 Pfizer & Co C 2-guanidino-1, 2, 3, 4-tetrahydronaphthalene and salts thereof
US3972932A (en) * 1973-11-09 1976-08-03 Akzona Incorporated Novel 2,6-disubstituted phenyl-aminoguanidine compounds
US4101675A (en) * 1973-11-09 1978-07-18 Akzona Incorporated Novel 2,6-di-substituted phenyl-aminoquanidine containing compositions and methods of using same and pharmaceutical compositions containing the same and therapeutic method
US4661520A (en) * 1984-08-17 1987-04-28 The Dow Chemical Company Cyanoguanidine useful as an animal growth promoting agent
US4689348A (en) * 1984-08-17 1987-08-25 Dow Chemical Company Cyanoguanidines useful as animal growth promoting agents
CN103664700A (en) * 2013-12-19 2014-03-26 浙江普康化工有限公司 Synthesis method for 1-ethyl-3-(3-dimethyl amino propyl)-carbonized diimine A iodate

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3344186A (en) * 1964-03-03 1967-09-26 Pfizer & Co C 2-guanidino-1, 2, 3, 4-tetrahydronaphthalene and salts thereof
US3972932A (en) * 1973-11-09 1976-08-03 Akzona Incorporated Novel 2,6-disubstituted phenyl-aminoguanidine compounds
US4101675A (en) * 1973-11-09 1978-07-18 Akzona Incorporated Novel 2,6-di-substituted phenyl-aminoquanidine containing compositions and methods of using same and pharmaceutical compositions containing the same and therapeutic method
US4661520A (en) * 1984-08-17 1987-04-28 The Dow Chemical Company Cyanoguanidine useful as an animal growth promoting agent
US4689348A (en) * 1984-08-17 1987-08-25 Dow Chemical Company Cyanoguanidines useful as animal growth promoting agents
CN103664700A (en) * 2013-12-19 2014-03-26 浙江普康化工有限公司 Synthesis method for 1-ethyl-3-(3-dimethyl amino propyl)-carbonized diimine A iodate
CN103664700B (en) * 2013-12-19 2016-06-22 浙江普康化工有限公司 A kind of 1-ethyl-3-(3-dimethylaminopropyl) synthetic method of-carbodiimides methiodide salt

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