GB783067A - Improvements in the production of 1-aminobenzophenone-sulphone-2-carboxylic acids ortheir esters - Google Patents

Improvements in the production of 1-aminobenzophenone-sulphone-2-carboxylic acids ortheir esters

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Publication number
GB783067A
GB783067A GB10398/56A GB1039856A GB783067A GB 783067 A GB783067 A GB 783067A GB 10398/56 A GB10398/56 A GB 10398/56A GB 1039856 A GB1039856 A GB 1039856A GB 783067 A GB783067 A GB 783067A
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GB
United Kingdom
Prior art keywords
sulphone
acid
give
nitro
isoxazole
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
GB10398/56A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB783067A publication Critical patent/GB783067A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1 - Aminobenzophenone - sulphone - 2 - carboxylic acids or their esters are made by nitrating a 2-methyl-benzophenone-sulphone, converting the 1-nitro-2-methylbenzophenone-sulphone to the isoxazole, and reacting the latter with (a) water, followed, if desired, by esterification of the resulting carboxylic acid, or with (b) an organic hydroxy compound, to give an ester direct. The last stage is preferably carried out in acid or alkaline medium. Non-reacting substituents specified are alkyl, halogen, nitro, alkyl sulphonyl. The nitration step may effect dias well as mono-nitration, and esterification may be by way of the acid chlorides or by way of the isatoic acid anhydrides. Conversion to the isoxazole may be effected with oleum of 60-65 per cent sulphur trioxide content. The products dye cellulose acetate, nylon, polyurethanes, and polyesters. In examples: (1) 2 - methylbenzophenone - sulphone is nitrated using potassium nitrate and sulphuric acid, the 1 - nitro - 2 - methyl - benzophenone - sulphone so obtained is converted to the isoxazole with oleum, and the isoxazole is either (a) heated with caustic soda solution to give 1-aminobenzophenone - sulphone - 2 - carboxylic acid, or (b) heated with potassium cyanide in ethanol to give the carboxylic ester; the ethanol may be replaced by n-butanol; (2) the 1-aminobenzophenone - sulphone - 2 - carboxylic acid obtained under (1) is treated with phosgene in nitrobenzene to give the isatoic acid anhydride which is reacted with ethylene glycol or phenol to give the corresponding esters; (3) the 1-nitro-2-methylbenzophenone-sulphone is further nitrated with nitrating acid and two dinitro bodies separately obtained, converted to the nitroisoxazoles, and these isoxazoles heated with caustic soda solution to obtain the acid.ALSO:1 - Aminobenzophenone - sulphone - 2 - carboxylic acids or their esters are made by nitrating a 2 - methylbenzophenone - sulphone, converting the 1 - nitro - 2 - methylbenzophenonesulphone to the isoxazole, and reacting the latter with (a) water, followed, if desired, by esterification of the resulting carboxylic acid, or with (b) an organic hydroxy compound to give an ester direct. The last stage is preferably carried out in acid or alkaline medium. Non-reacting substituents specified are alkyl, halogen, nitro, alkyl sulphonyl. The nitration step may effect dias well as mononitration, and esterification may be by way of the acid chlorides or by way of the isatoic acid anhydrides. Conversion to the isoxazole may be effected with oleum of 60-65 per cent sulphur trioxide content. The products dye cellulose acetate, nylon, polyurethanes and polyesters. In examples: (1) 2-methylbenzophenone-sulphone is nitrated using potassium nitrate and sulphuric acid, the 1-nitro - 2 - methyl - benzophenone - sulphone so obtained is converted to the isoxazole with oleum, and the isoxazole is either (a) heated with caustic soda solution to give 1-aminobenzophenone - sulphone - 2 - carboxylic acid; or (b) heated with potassium cyanide in ethanol to give the carboxylic ester; the ethanol may be replaced by n-butanol; (2) the 1-aminobenzophenone - sulphone - 2 - carboxylic acid obtained under (1) is treated with phosgene in nitrobenzene to give the isatoic acid anhydride which is reacted with ethylene glycol or phenol to give the corresponding esters; (3) the 1-nitro - 2 - methylbenzophenone - sulphone is further nitrated with nitrating acid and two dinitro bodies separately obtained, converted to the nitro-isoxazoles, and these isoxazoles heated with caustic soda solution to obtain the acids. 2 - Methyl - benzophenone - sulphone is prepared by condensation of thio- or dithio-salicylic acid with toluene in concentrated sulphuric acid to form the 2-methylthioxanthone and oxidation of the latter with hydrogen peroxide in acetic acid or a persulphate in sulphuric acid.
GB10398/56A 1955-04-06 1956-04-05 Improvements in the production of 1-aminobenzophenone-sulphone-2-carboxylic acids ortheir esters Expired GB783067A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE783067X 1955-04-06

Publications (1)

Publication Number Publication Date
GB783067A true GB783067A (en) 1957-09-18

Family

ID=6696036

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10398/56A Expired GB783067A (en) 1955-04-06 1956-04-05 Improvements in the production of 1-aminobenzophenone-sulphone-2-carboxylic acids ortheir esters

Country Status (1)

Country Link
GB (1) GB783067A (en)

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