GB436516A - Manufacture of sulphonic acid and carboxylic acid derivatives of 1:3-diaryl-5-pyrazolones - Google Patents

Manufacture of sulphonic acid and carboxylic acid derivatives of 1:3-diaryl-5-pyrazolones

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Publication number
GB436516A
GB436516A GB6979/34A GB697934A GB436516A GB 436516 A GB436516 A GB 436516A GB 6979/34 A GB6979/34 A GB 6979/34A GB 697934 A GB697934 A GB 697934A GB 436516 A GB436516 A GB 436516A
Authority
GB
United Kingdom
Prior art keywords
sulphophenylhydrazine
ester
pyrazolone
yield
sulphophenyl
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
GB6979/34A
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
Publication of GB436516A publication Critical patent/GB436516A/en
Expired legal-status Critical Current

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Classifications

    • EFIXED CONSTRUCTIONS
    • E05LOCKS; KEYS; WINDOW OR DOOR FITTINGS; SAFES
    • E05BLOCKS; ACCESSORIES THEREFOR; HANDCUFFS
    • E05B35/00Locks for use with special keys or a plurality of keys ; keys therefor
    • E05B35/003Locks for use with special keys or a plurality of keys ; keys therefor for keys with movable bits
    • E05B35/005Locks for use with special keys or a plurality of keys ; keys therefor for keys with movable bits pivoting about an axis parallel to the main key axis

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

Abstract

1 : 3-Diaryl-5-pyrazolones, substituted with at least one sulphonic or carboxylic group or both in at least one of the aryl radicles, are prepared by subjecting to ring closure the hydrazones obtained from correspondingly substituted arylhydrazines and aroylacetic esters. The production of the hydrazone and the ring closure are effected in an aqueous medium, and may be conducted without isolation of the hydrazone; the production of the hydrazone is preferably effected in an acid medium, and the ring closure in an alkaline medium. In the examples, (1) benzoylacetic ester is condensed (a) with 2-sulphophenylhydrazine, yielding 1 - (2<1> - sulphophenyl) - 3-phenyl-5-pyrazolone, and (b) with 3-sulphophenylhydrazine, 4 - sulphophenylhydrazine, 2-chloro-4-sulphophenylhydrazine, 2-chloro-5-sulphophenylhydrazine, 3 : 4-dichloro-6-sulphophenylhydrazine, 2-hydroxy-3-carboxy-5-sulphophenylhydrazine, 2-methyl-4-sulphophenylhydrazine 4 - carboxyphenylhydrazine, 4<1>-hydroxy-3<1>-carboxy-4-sulpho-1 : 1<1>-diphenylsulphone - 2 - hydrazine, 3 - methyl - 4 - chloro - 6-sulphophenylhydrazine, 2 : 5-dichloro-4-sulphophenylhydrazine, 1-sulpho-2-naphthylhydrazine, 4-nitro-2-sulphophenylhydrazine, 2-nitro-4-sulphophenylhydrazine, 2 : 5-disulphophenylhydrazine, and 2-methyl-4 : 5-disulphophenylhydrazine, yielding the corresponding 1-aryl-3-phenyl-5-pyrazolones; (2) p-chlorobenzoylacetic ester is condensed with 3-sulphophenylhydrazine, yielding 1-(3<1>-sulphophenyl)-3-(4<1>-chlorophenyl)-5-pyrazolone; (3) m-nitrobenzoylacetic ester and 2-sulphophenylhydrazine yield 1-(2<1>-sulphophenyl)-3-(3<1>-nitrophenyl)-5-pyrazolone; (4) 4-methylbenzoylacetic ester and 2-chloro-5-sulphophenylhydrazine yield 1-(2<1>-chloro-5<1>-sulphophenyl) - 3 - (4<1> - methylphenyl) - 5 - pyrazolone; (5) 4-methoxybenzoylacetic ester and 2-hydroxy-3-carboxy-5-sulphophenylhydrazine yield 1 - (2<1> - hydroxy - 3<1> - carboxy - 5<1> - sulphophenyl) - 3 - (4<1> - methoxyphenyl) - 5 - pyrazolone; (6) 2 : 4-dichlorobenzoylacetic ester and 4-sulphophenylhydrazine yield 1-(4<1>-sulphophenyl)-3 - (2<1> : 4<1> - dichlorophenyl) - 5 - pyrazolone; (7) a -naphthoylacetic ester and 1-sulpho-2-naphthylhydrazine yield 1-(2<1>-naphthyl-1<1>-sulpho)-3 - (1<1> - naphthyl) - 5 - pyrazolone; (8) b -naphthoylacetic ester and 3 : 4-dichloro-6-sulphophenylhydrazine yield 1-(3<1> : 4<1>-dichloro-6<1>-sul phophenyl) - 3 - (2<1> - naphthyl) - 5 - pyrazolone; (9) 4-phenylbenzoylacetic ester and 3-sulphophenylhydrazine yield 1-(3<1>-sulphophenyl)-3-(4<1> - diphenyl) - 5 - pyrazolone; (10) 4-carboxybenzoylacetic ester is condensed (a) with 2 - chloro - 5 - sulphophenylhydrazine, yielding 1-(2<1>-chloro-- 5<1>-sulphophenyl) - 3 - (4<1> - carboxyphenyl)-5-pyrazolone, and (b) with 4-sulphophenylhydrazine, 2-sulphophenylhydrazine, phenylhydrazine, m-carboxyphenylhydrazine, 2-hydroxy-3-carboxy-5-sulphophenylhydrazine, 1 - sulpho - 2 - naphthylhydrazine, and 4-nitrophenylhydrazine, yielding the corresponding 1 - aryl - 3 - (4<1>-carboxyphenyl) - 5 - pyrazolones; (11) m-chlorobenzoylacetic ester and 4 - nitro-2-sulphophenylhydrazine yield 1-(4<1>-nitro-2<1>-sulphophenyl) - 3 - (3<1> - chlorophenyl) - 5 - pyrazolone; (12) 4-nitrobenzoylacetic ester and 2-nitro-4-sulphophenylhydrazine yield 1-(2<1>-nitro - 4<1> - sulphophenyl) - 3 - (4<1> - nitrophenyl)-5-pyrazolone. Hydrazines.--The arylhydrazines specified above are obtainable by treating the diazo compounds of the corresponding bases with sodium sulphite, reducing the diazosulphonates so obtained with sulphurous acid or zinc dust, and saponifying the resulting hydrazinesulphonates with an inorganic acid; alternatively, the diazo compounds may be reduced directly to the hydrazines with stannous chloride. Aroylacetic esters.--p - Carboxybenzoylacetic acid ethyl ester is obtainable by treating a terephthalic acid monoalkyl ester with thionyl chloride to yield the mono-acid chloride, condensing this with acetoacetic ester to yield the corresponding aroylacetoacetic ester, splitting off the acetyl group, for instance with ammonia, and saponifying the ester group attached to the benzene ring with alcoholic caustic alkali. The other aroylacetic esters specified above are similarly obtainable from the corresponding aroyl chloride and acetoacetic ester. The Specification as open to inspection under Sect. 91 describes the preparation of 1-(4<1>-diphenyl - 4<11> - sulpho) - 3 - phenyl - 5 - pyrazolone from 4<1> - sulpho - 4 - diphenylhydrazine and benzoylacetic acid ethyl ester. This subject-matter does not appear in the Specification as accepted.
GB6979/34A 1933-03-03 1934-03-05 Manufacture of sulphonic acid and carboxylic acid derivatives of 1:3-diaryl-5-pyrazolones Expired GB436516A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE436516X 1933-03-03

Publications (1)

Publication Number Publication Date
GB436516A true GB436516A (en) 1935-10-07

Family

ID=6506910

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6979/34A Expired GB436516A (en) 1933-03-03 1934-03-05 Manufacture of sulphonic acid and carboxylic acid derivatives of 1:3-diaryl-5-pyrazolones

Country Status (2)

Country Link
FR (1) FR436516A (en)
GB (1) GB436516A (en)

Also Published As

Publication number Publication date
FR436516A (en) 1912-03-29

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