GB604032A - Improvements relating to the manufacture of amidines - Google Patents

Improvements relating to the manufacture of amidines

Info

Publication number
GB604032A
GB604032A GB3136245A GB3136245A GB604032A GB 604032 A GB604032 A GB 604032A GB 3136245 A GB3136245 A GB 3136245A GB 3136245 A GB3136245 A GB 3136245A GB 604032 A GB604032 A GB 604032A
Authority
GB
United Kingdom
Prior art keywords
product
benzenesulphonate
heated
hydrochloride
ammonium
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
GB3136245A
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.)
Boots Pure Drug Co Ltd
Original Assignee
Boots Pure Drug Co 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 Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Priority to GB3136245A priority Critical patent/GB604032A/en
Publication of GB604032A publication Critical patent/GB604032A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Compounds containing the amidine group are manufactured by heating a nitrile of the general formula R.CN (wherein R represents an alkyl, aryl, aralkyl, alicyclic or heterocyclic group, which groups may contain substituents) with a compound of the general formula NHR1R2 (wherein R1 and R2 each represent hydrogen or an alkyl, aralkyl or alicyclic radical) in the presence of a salt of ammonia, a primary, secondary of tertiary alkylamine, aralkylamine or alicyclic amine or a tertiary aryl of heterocyclic -amine. The compound NHR1R2 may be replaced by a compound NR1R2.CO.NH2, which acts as a source thereof under the reaction conditions, whilst the ammonium or amine salt employed may be formed in situ by the reaction of an acid with ammonia or an amine of the stated type or a substance which acts as a source thereof. In examples: (1) benzyl cyanide is heated with ammonium benzenesulphonate while passing in ammonia gas, producing phenylacetamidine benzenesulphonate; (2) p-methylsulphonylbenzonitrile is heated with ammonium methanesulphonate or ammonium chloride while passing in ammonia gas, the the product is treated with ammonium benzenesulphonate solution to form p - methylsulphonylbenzamidine benzenesulphonate; (3) the same product is obtained by treating p-methylsulphonylbenzonitrile as in (1); (4) the ammonium salt in (2) is replaced by ammonium thiocyanate, and the product is isolated as hydrochloride; (5) p-nitrobenzonitrile is treated as in (1) to give p-nitrobenzamidine benzenesulphonate; (6) 3 : 5-dinitrobenzonitrile similarly yields 3 : 5-dinitrobenzamidine benzenesulphonate; (7) p-methylsulphonylbenzonitrile is heated with dimethylamine benzenesulphonate while passing in ammonia gas, yielding the product of (2); (8) p : p1 - dicyano - a : g - diphenoxypropane is treated as in (1) and the product is worked up to give p : p1 - diamidino - a : g - diphenoxypropane dihydrochloride; (9) p-methylsulphonylbenzonitrile is heated with urea and ammonium benzenesulphonate and the product is treated with sodium hydroxide solution to liberate p - methylsulphonylbenzamidine; (10) p-nitrobenzonitrile is heated with urea and benzenesulphonic acid hydrate, and the product is converted, via the free base, into p-nitrobenzamidine picrate; (11) 2 - cyanopyridine is treated as in (9) and the product is converted, via the free base, into 2-amidinopyridine picrate; (12) n-heptyl cyanide is heated with cyclohexylamine and its toluene-p-sulphonate, and the product is converted, via the free base, into N-cyclohexylcaprylamidine hydrochloride; (13) benzyl cyanide is heated with cyclohexylamine and its hydrochloride to form N-cyclohexylphenylacetamidine hydrochloride; (14) the cyclohexylamine hydrochloride in (13) is replaced by ammonium chloride; (15) the cyclohexylamine hydrochloride in (13) is replaced by pyridine benzenesulphonate, and the product is converted, via the free base, into its hydrochloride; (16) p-methylsulphonylbenzonitrile is heated with ammonium benzenesulphonate while passing in dry dimethylamine, and the product is converted, via the free base, into N : N-dimethyl - p - methylsulphonyl benzamidine hydrochloride; (7) p-methylsulphonylbenzonitrile is heated with N : N-dimethylurea and dimethylamine hydrochloride, and the product is converted, via the free base, into N : N-dimethyl - p - methylsulphonylbenzamidine picrate.
GB3136245A 1945-11-21 1945-11-21 Improvements relating to the manufacture of amidines Expired GB604032A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3136245A GB604032A (en) 1945-11-21 1945-11-21 Improvements relating to the manufacture of amidines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3136245A GB604032A (en) 1945-11-21 1945-11-21 Improvements relating to the manufacture of amidines

Publications (1)

Publication Number Publication Date
GB604032A true GB604032A (en) 1948-06-28

Family

ID=10321972

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3136245A Expired GB604032A (en) 1945-11-21 1945-11-21 Improvements relating to the manufacture of amidines

Country Status (1)

Country Link
GB (1) GB604032A (en)

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