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Synthesis of 2‐oxo and 2‐thioxo‐3(2 H )‐benzothiazoleethanimic acid anhydride with acetic acid and related products
Author(s) -
D'Amico John J.,
Bellinger Frederic G.,
Freeman John J.
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250547
Subject(s) - chemistry , acetic anhydride , catalysis , acetic acid , organic chemistry , nitrile , salt (chemistry) , ammonium acetate , sodium hydroxide , ammonia , medicinal chemistry , high performance liquid chromatography
The reaction of the appropriate 2‐benzothiazolinone with 2‐chloroacetamide under basic conditions afforded the 2‐oxo‐3(2 H )‐benzothiazolineacetamides 6–9. The 2‐thioxo‐3(2 H )‐benzothiazolineacetamide ( 10 ) was prepared by the reaction of 3‐(carbethoxymethyl)benzothiazoline‐2‐thione with ammonium hydroxide. The reaction of acetamides 6–10 with the appropriate anhydride containing a catalytic amount of the sodium salt of the acid corresponding to the anhydride afforded the titled compounds 11–18 in excellent yields. The omission of the catalyst in the same reaction furnished a mixture containing 57% of the titled compound, 37% of the nitrile and 6% of an unknown. Possible mechanism and supporting nmr, ir and mass spectral data are discussed.