Thiocarbamates and their derivatives

Details Thiocarbamates and their derivatives Thiocarbamates and their derivatives

1986-06-17

1992-10-20

Lee, Mary C.

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

Organic compounds

Esters having the thiocarboxylate group, -cx-, wherein the...

C07C33300

Patent

active

051571420

ABSTRACT:
A process is provided for preparing N-acyl-aminothiophenols, e.g., N-acetyl-para-aminothiophenol, or aminothiophenols, e.g., para-aminothiophenol, by reacting a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone (4-HAP), with hydroxylamine or a hydroxylamine salt, to form the oxime of the ketone, subjecting the oxime to a Beckmann rearrangement in the presence of a catalyst to form the N-acyl-hydroxy aromatic amine, e.g., N-acetyl-para-aminophenol (APAP), reacting the N-acyl-hydroxy aromatic amine with an N,N-di (organo) thiocarbamoyl halide, e.g., N,N-dimethylthiocarbamoyl chloride, to form an O-(N-acyl-aminoaryl)-N,N-di (organo) thiocarbamate, e.g., O-(N-acetyl-para-aminophenyl)-N,N-dimethylthiocarbamate, pyrolytically rearranging the O-(N-acyl-aminoaryl)-N,N-di (organo) thiocarbamate to form an S-(N-acyl-aminoaryl)-N,N-di (organo) thiocarbamate, e.g., S-(N-acetyl-para-aminophenyl)-N,N-dimethylthiocarbamate, and hydrolyzing the latter compound to obtain the N-acyl aminothiophenol or aminothiophenol. The N-acyl aminothiophenol may be reacted with an acylating agent to form the N,S-diacyl-aminothiophenol, e.g., N,S-diacetyl-p-aminothiophenol, or may be further hydrolyzed to the aminothiophenol, e.g., p-aminothiophenol.

REFERENCES:
patent: 3476791 (1969-11-01), Newman et al.
patent: 4524217 (1985-06-01), Davenport et al.
Chem. Ber., vol. 58, 1925, pp. 36-51.
Synthetic Communications, 13(11), 941-944(1983).
Pearson et al., J. Am. Chem. Soc., Dec. 1953, pp. 5905-5908.
Newman et al., J. Org. Chemistry, vol. 31, pp. 3980-3984 (1966).
Kwart et al., J. Org. Chemistry, vol. 31, pp. 410-413 (1966).
Reid, Organic Chemistry of Bivalent Sulfur, vol. IV, p. 201, 1962, Chemical Publishing Co. Inc., NY.

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