GB800869A - Substituted amino-guanidines - Google Patents
Substituted amino-guanidinesInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives 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
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives 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
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds 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.
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)
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 |
-
1955
- 1955-09-28 GB GB2760355A patent/GB800869A/en not_active Expired
Cited By (7)
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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