Preparation of 2-halo-3-nitro-5-acyl thiophenes and intermediate

Details Preparation of 2-halo-3-nitro-5-acyl thiophenes and intermediate Preparation of 2-halo-3-nitro-5-acyl thiophenes and intermediate

1981-04-24

1982-12-28

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 75, C07D33300, C07D33324

Patent

active

043663214

ABSTRACT:
Disclosed are novel intermediates and their preparation, and the preparation therefrom of 2-halo-3-nitro-5-acyl thiophenes which themselves are important intermediates for the preparation of azo dyes of the type, ##STR1## wherein C.sup.1 represents typically any aniline, tetrahydroquinoline, benzomorpholine or the like coupler and the acyl group contains from 1-10 carbons. It has been found that if 2-acyl thiophene is treated with a hydroxylamine compound, e.g., a salt of hydroxylamine, including sulphate, chloride or the like, to form the oxime prior to the 2-position halogenation and 3-position nitration steps, various side reactions such as halogenation of the acyl group and nitration of the 5-position are avoided, the yield of each step is improved, and the reactions are less sensitive to the deleterious effects of temperature variations and excess reactants. The oxime derivative is readily reconverted to the acyl derivative after the halogenation and nitration steps have been completed. This product is then readily aminated to give the 2-amino derivative.

REFERENCES:
patent: 2649461 (1953-08-01), Hermann
patent: 3822314 (1974-07-01), Gay et al.
patent: 4158015 (1979-06-01), Paul
patent: 4188203 (1980-02-01), Farge et al.

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