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Derivatives of 3‐(2‐hydroxyethyl)2‐benzothiazolinone and related compounds
Author(s) -
D'Amico John J.,
Bellinger Frederic G.
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.5570250601
Subject(s) - chemistry , potassium hydroxide , acetic acid , halogen , organic chemistry , disulfide bond , potassium , tetrabutylammonium hydroxide , alkyl , biochemistry
The reaction of the appropriate 2‐benzothiazolinone with 2‐chloroethanol or 3‐chloropropanol under basic conditions afforded 3‐(2‐hydroxyethyl or 3‐hydroxypropyl)‐2‐benzothiazolinone and related compounds 1–7. The reaction of the alcohols 1,4, 5 or 7 with potassium hydroxide and excess carbon disulfide furnished the potassium salts of xanthic acid 8–11 which upon oxidation gave the disulfides 12–15. Esters of xanthic acid 16–23 were prepared by the reaction of 8 or 11 with various halogen compounds. Esters of acetic acid 24–28 were prepared by the reaction of the appropriate 2‐benzothiazolinone with 2‐bromoethyl acetate under basic conditions. Esterification of 1 with various acids afforded the esters 25, 29–32.