Dimethylformamide → HCID 178457774, compound

Participants

Reaction Conditions

Reaction Steps

Cyanoacetic acid (1.63 g, 19.17 mmol) was suspended in anhydrous dichloromethane (40 ml). A catalytic amount of N,N-dimethylformamide (0.1 ml) was added and the mixture cooled to 0° C. under an atmosphere of Argon. After 20 minutes stirring at 0° C., oxalyl chloride (1.67 ml, 19.17 mmol) was slowly added to the reaction mixture, which was then allowed to warm to ambient temperature. This mixture was added slowly, after stirring 1 hour, to a 1 M solution of 6-isopropylamino-1,3-benzothiazole-2-thiol (2.16 g, 9.57 mmol) in anhydrous pyridine. After 2 hours the reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and 1 M aqueous citric acid. The resulting precipitate was collected by filtration, combined with the organic extract and concentrated in vacuo. The residue was triturated with diethyl ether to yield 2.32 g (83%). 1H NMR (DMSO-d6) δ=0.98 (m, 6H), 3.43 (s, 2H), 4.75 (sep, 1H), 7.27 (d, 1H), 7.35 (d, 1H), 7.63 (s, 1H), 13.94 (s, 1H); ESIMS: m/z290 (M-H).

Provenance & Evidence