GB446532A - Manufacture of aminotrifluoromethyl-aryl-sulphonic acids - Google Patents

Manufacture of aminotrifluoromethyl-aryl-sulphonic acids

Info

Publication number
GB446532A
GB446532A GB3149734A GB3149734A GB446532A GB 446532 A GB446532 A GB 446532A GB 3149734 A GB3149734 A GB 3149734A GB 3149734 A GB3149734 A GB 3149734A GB 446532 A GB446532 A GB 446532A
Authority
GB
United Kingdom
Prior art keywords
amino
trifluoromethylbenzene
sulphonic acid
benzotrifluoride
chloro
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
GB3149734A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB3149734A priority Critical patent/GB446532A/en
Publication of GB446532A publication Critical patent/GB446532A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Amino-trifluoromethyl-aryl sulphonic acids are prepared by treating amino-trifluoromethylaryl compounds with chlorsulphonic acid. The reaction may be effected with an excess of chlorsulphonic acid at atmospheric or raised temperature, or with equimolecular proportions of the reagents in an inert organic solvent at a raised temperature; halogenated hydrocarbons (several specified) and nitrobenzene are suitable solvents. Examples are given in which the following sulphonic acids are prepared from the corresponding unsulphonated compounds and chlorsulphonic acid: 1-amino-3-trifluoromethylbenzene-4-sulphonic acid; 1-amino-4-trifluoromethylbenzene - 2 - sulphonic acid; 1-amino-2-trifluoromethylbenzene-4-sulphonic acid; 1-amino-2-chloro-5-trifluoromethylbenzene - 4 - sulphonic acid; 1 - amino - 2 : 4-dichloro - 5 - trifluoromethylbenzene-6-sulphonic acid; 1-amino-2 : 5-dichloro-3-trifluoromethylbenzene-4-sulphonic acid; 1-amino-2-bromo-5-trifluoromethylbenzene-4-sulphonic acid; 1-amino - 4 - chloro - 2 - trifluoromethylbenzene - 6-sulphonic acid; 1-amino-4-chloro-3-trifluoromethylbenzene-6-sulphonic acid; 1-amino-2-methoxy-5-trifluoromethylbenzene-4-sulphonic acid; 1 - amino - 4 - methoxy - 5 - trifluoromethylbenzene-2-sulphonic acid; 1-amino-2-ethoxy-5-trifluoromethylbenzene - 4 - sulphonic acid; 1-amino - 4 - phenoxy - 5 - trifluoromethylbenzene-2-sulphonic acid; 1 - amino - 2 - benzyloxy - 5 - trifluoromethylbenzene - 4 - sulphonic acid; 1-amino - 2 : 4 - dimethoxy - 5 - trifluoromethylbenzene-6-sulphonic acid; 1-amino-2-nitro-4-trifluoromethylbenzene - 6 - sulphonic acid; 1 amino - 2 - nitro - 5 - trifluoromethylbenzene - 4 - sulphonic acid; 1 - amino - 4 - nitro - 5 - trifluoromethylbenzene - 2 - sulphonic acid; 1-amino - 3 : 5 - bis - trifluoromethylbenzene - 4 - sulphonic acid; 1-amino-2 : 5-bis-trifluoromethylbenzene-4-sulphonic acid; 1-amino-2-chloro-3 : 5 - bis - trifluoromethylbenzene - 4 - sulphonic acid; 1 - amino - 5 - trifluoromethylbenzene - 2 - ethylsulphone-4-sulphonic acid; 1-amino-3-trifluoromethylbenzene - 4 - methylsulphone - 6 - sulphonic acid; 1-amino-2-trifluoromethylbenzene - 4 - phenylsulphone - 6 - sulphonic acid; and 1 - amino - 5 - trifluoromethylbenzene - 2-benzylsulphone-4-sulphonic acid. Amino-trifluoromethyl-aryl compounds. Particulars of the preparation of various starting materials, used in making the products specified above, are given as follows: 1-Amino-2- and -4-nitro-5-trifluoromethylbenzenes are prepared from 1-acetylamino-3-trifluoromethylbenzene, which is nitrated to yield a mixture of 1-acetylamino-2- and -4-nitro-5-trifluoromethylbenzenes; the acetyl group is saponified and the nitroamine mixture is separated into its components by steam distillation. 1-Amino-2- and -4-trifluoromethylbenzenes are prepared from 1-amino-2- and -4-nitro-5-trifluoromethylbenzenes by deamination followed by reduction. 1 - Amino - 2 : 4 - dichloro - 5 - benzotrifluoride is prepared from 2 : 4-dichlorobenzotrichloride by heating with antimony trifluoride to form 2 : 4-dichlorobenzotrifluoride, which is then nitrated and reduced (cf. Specification 361,097). 1 - Amino - 2 : 5 - dichloro - 3 - benzotrifluoride is prepared similarly from 2 : 5-dichlorobenzotrichloride. 1-Amino-2-bromo-5-benzotrifluoride is prepared similarly from 4-bromobenzotrichloride. 1-Amino-4-chloro-2-benzotrifluoride is obtainable similarly from 3-chlorobenzotrichloride. 1-Amino-4-chloro-3-benzotrifluoride is obtainable similarly from 2-chlorobenzotrichloride. 1-Amino-4-methoxy-5-benzotrifluoride is prepared by converting 4-chloro-5-benzotrichloride, by the reactions indicated in Specification 361,097, into 1-nitro-4-chloro-5-benzotrifluoride, in which the chlorine atom is then replaced by the methoxy group and the nitro group is reduced. 1 - Amino - 2 - ethoxy - 5 - benzotrifluoride, 1-amino-4-phenoxy-5-benzotrifluoride, 1-amino-2-benzyloxy-5-benzotrifluoride and 1-amino-2 : 4-dimethoxy - 5 - benzotrifluoride are obtained similarly from the corresponding nitrochlorobenzotrifluorides. 1-Amino-3 : 5-bis-trifluoromethylbenzene is prepared by treating 1 : 3-bis-trichloromethylbenzene with anhydrous hydrogen fluoride, and subjecting the product to nitration and reduction (cf. French Specification 745,293). 1 - Amino - 2 : 5 - bis - trifluoromethylbenzene and 1-amino-2-chloro-3 : 5-bis-trifluoromethylbenzene are similarly obtainable. 1 - Amino - 5 - trifluoromethylbenzene - 2 - ethylsulphone is prepared by condensing 1-nitro-2-chloro-5-benzotrifluoride with the sodium salt of ethanesulphinic acid, and reducing the nitro group in the product. 1-Amino- 3 -trifluoromethylbenzene - 4 - methylsulphone, 1-amino-2-trifluoromethylbenzene-4-phenylsulphone, and 1-amino-5-trifluoromethylbenzene-2-benzylsulphone are obtainable similarly from the corresponding nitrochlorobenzotrifluorides. Specification 440,207 also is referred to.
GB3149734A 1934-11-02 1934-11-02 Manufacture of aminotrifluoromethyl-aryl-sulphonic acids Expired GB446532A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3149734A GB446532A (en) 1934-11-02 1934-11-02 Manufacture of aminotrifluoromethyl-aryl-sulphonic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3149734A GB446532A (en) 1934-11-02 1934-11-02 Manufacture of aminotrifluoromethyl-aryl-sulphonic acids

Publications (1)

Publication Number Publication Date
GB446532A true GB446532A (en) 1936-05-01

Family

ID=10323960

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3149734A Expired GB446532A (en) 1934-11-02 1934-11-02 Manufacture of aminotrifluoromethyl-aryl-sulphonic acids

Country Status (1)

Country Link
GB (1) GB446532A (en)

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