GB587810A - Improvements relating to the production of substituted carboxylic amides - Google Patents

Improvements relating to the production of substituted carboxylic amides

Info

Publication number
GB587810A
GB587810A GB142945A GB142945A GB587810A GB 587810 A GB587810 A GB 587810A GB 142945 A GB142945 A GB 142945A GB 142945 A GB142945 A GB 142945A GB 587810 A GB587810 A GB 587810A
Authority
GB
United Kingdom
Prior art keywords
acid
methyl
prepared
heating
organic
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
GB142945A
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 Co PLC
Boots Pure Drug Co Ltd
Original Assignee
Boots Co PLC
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 Co PLC, Boots Pure Drug Co Ltd filed Critical Boots Co PLC
Priority to GB142945A priority Critical patent/GB587810A/en
Publication of GB587810A publication Critical patent/GB587810A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms

Abstract

N.N-Disubstituted carboxylic acid amides are obtained by heating a carboxylic acid, e.g. at 200-250 DEG C. with an organic sulphondialkylamide of the general formula R.SO2.N.R.1R2, where R.SO2 is the residue of an organic sulphonic acid and R1 and R2 are the same or different straight or branched chain alkyl groups including methyl groups or may together constitute a divalent polymethylene group which forms with the nitrogen atom a heterocyclic ring. In cases when the carboxylic acid contains a ring nitrogen atom or other basic atom or group, the yield may be improved by treating either the acid alone or the reaction mixture with another acid prior to or at any early stage in the reaction with the organic sulphondialkylamide. In examples: (1) N.N-dimethylbenzamide is obtained by heating benzoic acid with benzenesulphondimethylamide; nicotinic acid diethylamide is obtained by heating (2) nicotinic acid with benzenesulphondiethylamide, (3) nicotinic acid benzenesulphonate with benzenesulphondiethylamide. Samples have been furnished under Sect. 2 (5) of: N-methyl-N-ethylchloracetamide prepared from chloracetic acid N-methyl-N-ethylbenzene-sulphonamide; N - methyl - N - n - propylbenzamide prepared from benzoic acid and N-methyl-N-n-propylbenzenesulphonamide; N-benzoylpiperidine prepared from benzoic acid and N-toluene-p-sulphonylpiperidine.
GB142945A 1945-01-17 1945-01-17 Improvements relating to the production of substituted carboxylic amides Expired GB587810A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB142945A GB587810A (en) 1945-01-17 1945-01-17 Improvements relating to the production of substituted carboxylic amides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB142945A GB587810A (en) 1945-01-17 1945-01-17 Improvements relating to the production of substituted carboxylic amides

Publications (1)

Publication Number Publication Date
GB587810A true GB587810A (en) 1947-05-06

Family

ID=9721874

Family Applications (1)

Application Number Title Priority Date Filing Date
GB142945A Expired GB587810A (en) 1945-01-17 1945-01-17 Improvements relating to the production of substituted carboxylic amides

Country Status (1)

Country Link
GB (1) GB587810A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681341A (en) * 1952-08-19 1954-06-15 S E Massengill Company Solid acid salts of nu, nu-diethyl pyridine-3-carboxylic acid amide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681341A (en) * 1952-08-19 1954-06-15 S E Massengill Company Solid acid salts of nu, nu-diethyl pyridine-3-carboxylic acid amide

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