The reaction of the appropriate 2‐benzothiazolinone with 2‐chloroacetamide under basic conditions afforded the 2‐oxo‐3(2H)‐benzothiazolineacetamides 6–9. The 2‐thioxo‐3(2H)‐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.

The reaction of the potassium salt of 2‐mercaptobenzimidazole with 3‐acetyl‐3‐chloropropyl acetate afforded the novel heterocyclic compound 1. When solutions of 1 in deuteriodimethylsulfoxide or deuteriomethanol were allowed to stand at room temperatures for 15 minutes and 19 days, respectively, ring opening of 1 occurred to give the precursor, 3‐acetyl‐3‐(2‐benzimidazolthio)propyl‐1‐ol. The treatment of 1 with p‐fluorophenyl isocyanate furnished the carbanilate 2. The reaction of ammonium dithiocarbamate with the above chloroketone afforded the 2‐thiazolethione 3. Possible mechanisms and supporting nmr, ir, mass spectral data for 1–3 and single crystal X‐ray analysis for 2 are discussed.

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.

The reaction of 3‐(2‐hydroxyethyl)‐2‐benzothiazoline with methyl, phenyl isocyanate, or dimethylcarbamoyl chloride afforded the carbamates 1–4. The carbanilate 5 was prepared by the reaction of 2‐benzothiazolinone with 3‐chloropropyl‐N‐methylcarbanilate under basic conditions. The reaction of the appropriate 2‐benzothiazolinone with the appropriate 2‐chloro or 3‐chloropropyl disubstituted thiolcarbamate under basic conditions furnished the thiolcarbamates 6–14. The thiolcarbamate 15 was prepared by the reaction of sodium di‐isopropylthiolcarbamate with 3‐(chloromethyl)‐2‐benzothiazolinone. The reaction of 3‐(chloromethyl)‐2‐ben‐zothiazolinone and related compound with the appropriate sodium or triethylamine salt of disubstituted dithiocarbamate afforded the dithiocarbamate 16–22. The reaction of the appropriate xanthate with the potassium salt of bromoacetic acid and the appropriate secondary amine afforded the thionocarbamates 23–29. The thionocarbamate 30 was synthesized by the reaction of 5‐chloro‐2‐benzothiazolinone with 3‐chloropropyl diethylthionocarbamate.