GB579303A - Improvements relating to the production of cyclic amidines or salts thereof - Google Patents

Improvements relating to the production of cyclic amidines or salts thereof

Info

Publication number
GB579303A
GB579303A GB1027744A GB1027744A GB579303A GB 579303 A GB579303 A GB 579303A GB 1027744 A GB1027744 A GB 1027744A GB 1027744 A GB1027744 A GB 1027744A GB 579303 A GB579303 A GB 579303A
Authority
GB
United Kingdom
Prior art keywords
benzenesulphonate
oxime
benzene
extracted
general formula
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
GB1027744A
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 GB1027744A priority Critical patent/GB579303A/en
Publication of GB579303A publication Critical patent/GB579303A/en
Expired legal-status Critical Current

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Amidines of the general formula:-<FORM:0579303/IV/1> or salts thereof, wherein R represents a chain of methylene or alkyl substituted methylene radicals and R1 and R2 are each a hydrocarbon radical or hydrogen, or one is a hydrocarbon radical and the other a hydrogen atom, are produced (a) by reaction of ammonia or a primary or secondary amine with a sulphonic ester of the general formula:- <FORM:0579303/IV/2> where R has the significance above and X is a hydrocarbon radical. The sulphonic ester is obtained by reaction of: (a) a lactam having the general formula:- <FORM:0579303/IV/3> or (b) a ketoxime of the general formula:- <FORM:0579303/IV/4> with a sulphonyl halide, R again representing a chain of methylene or alkyl-substituted methylene radicals. In examples: (1) benzenesulphonyl chloride is added to cyclohexanone oxime in 2.25 N. sodium hydroxide and acetone and the oxime benzenesulphonate is extracted with benzene and treated with aniline prior to adding caustic soda to liberate 2-phenyliminohexamethylene imine; (2) e -caprolactam in pyridine-benzene is stirred with benzene-sulphonyl chloride at room temperature and aniline is added, 2-phenyliminohexamethyleneimine being isolated from the aqueous extract as in (1); (3) 2-phenyl cyclopentanone is added to hydroxylamine hydrochloride in 4.45 N. sodium hydroxide and the resulting solution of sodium cyclopentanone oxime is cooled to about - 5 DEG C., benzenesulphonyl chloride is added, cyclopentanone oxime benzenesulphonate is benzene-extracted and reaction with aniline is effected prior to isolating 2-phenyliminopiperidine on adding caustic soda (4) cyclopentanone oxime benzenesulphonate prepared as in (3) is extracted with nitrobenzene ammonia being introduced into the stirred solution, and on warming to 80 DEG C. an exothermic reaction is initiated and 2-iminopiperidine benzenesulphonate is crystallized from the mixture; (5) cyclohexanone oxime benzenesulphonate prepared as in (4) is extracted with nitrobenzene, ammonia is introduced and the mother liquor, evaporated to dryness in vacuo, yields 2-iminohexamethyleneimine benzenesulphonate.
GB1027744A 1944-05-26 1944-05-26 Improvements relating to the production of cyclic amidines or salts thereof Expired GB579303A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1027744A GB579303A (en) 1944-05-26 1944-05-26 Improvements relating to the production of cyclic amidines or salts thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1027744A GB579303A (en) 1944-05-26 1944-05-26 Improvements relating to the production of cyclic amidines or salts thereof

Publications (1)

Publication Number Publication Date
GB579303A true GB579303A (en) 1946-07-30

Family

ID=9964878

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1027744A Expired GB579303A (en) 1944-05-26 1944-05-26 Improvements relating to the production of cyclic amidines or salts thereof

Country Status (1)

Country Link
GB (1) GB579303A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0212479A1 (en) * 1985-08-20 1987-03-04 Bayer Ag Use of lactam amides as efficiency improvers in animals

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0212479A1 (en) * 1985-08-20 1987-03-04 Bayer Ag Use of lactam amides as efficiency improvers in animals

Similar Documents

Publication Publication Date Title
Heine et al. The isomerization of some 1-aroylaziridines. II
GB579303A (en) Improvements relating to the production of cyclic amidines or salts thereof
Davis et al. 2-Arylsulphonyl-3-phenyloxaziridines: a new class of stable oxaziridine derivatives
US2086822A (en) Process for producing aromatic asymmetrical thiourea derivatives
GB679678A (en) Improvements in or relating to the production of 3-amino pyrazolines
US2647118A (en) Method for preparing bis-(substituted tetrahydro-1, 3-oxazino)-methanes
US2806036A (en) Process for preparation of
US2742475A (en) Azacycloalkanes
US1737192A (en) Diguanidine
US2513270A (en) Production of 2-iminopiperidines and 2-iminopyrrolidines
US3145229A (en) Process for the production of nu-substituted-1-phenylcyclohexylamines
GB577696A (en) Improvements relating to the production of lactams
GB577478A (en) Improvements relating to the manufacture of amidines
US2917545A (en) Preparation of n-substituted hydrazine derivatives
US2671798A (en) 2, 2-diphenyl-3-methyl-4-chlorobutyronitrile and processes for preparing the same
US2464004A (en) Stable quinoline salt for electrolysis
GB559015A (en) Improvements in or relating to the production of amidine salts
US3597444A (en) Method of synthesizing selenoureas from thioureas
US3631165A (en) Azatricyclic compounds
GB799780A (en) New n-alkyl-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-alkyl-pyrrolidine-ª‡-monocarboxylic acid amides
US2957002A (en) 6-lower alkyl carboxamidobenzothiazole-2-sulfonamide
US2386111A (en) Dithiofuroates
US2702801A (en) Conversion of secondary nitro compounds to amides
GB830630A (en) Improvements in the production of lactams from oxime hydrochlorides
GB512629A (en) Manufacture of dithiohydantoins