Hydroxylamine → HCID 19063896, compound

Participants

Reaction Conditions

Reaction Steps

0.88 g of hydroxylamine hydrochloide is added to a solution of 0.7 g of potassium hydroxide in 15 ml of methanol and the reaction mixture is brought to reflux for 10 minutes. 0.5 g of 2-chloro-6-(trifluoromethyl)benzothiazole is then added and reflux is continued for 8 hours. After cooling to a temperature in the region of 20° C., the insoluble material is filtered off, the filtrate concentrated to dryness and the residue taken up in dichloromethane. The organic phase is washed with water and then dried and concentrated to dryness under reduced pressure (15 mm Hg, 2 kPa). The crude product thus obtained is purified by flash chromatography on a silica column, an ethyl acetate/cyclohexane (40/60 by volume) mixture being used as eluent. 0.35 g of 2-hydroxyamino-6-(trifluoromethyl)benzothiazole is thus obtained in the form of an orangey powder, the melting point of which is greater than 260° C. (Analysis % calculated C: 41.03, H: 2.15, N: 11.96, S: 13.69; found C: 41.4, H: 1.6, N: 12.3, S: 13.9) [1H N.M.R. spectrum (200 MHz, d6-(CD3)2SO, δ in ppm): 7.2 (broad s, 1H, aromatic CH), 7.53 (d, J=7 Hz, aromatic CH, 8.0 (broad s, 1H, aromatic CH), 10.07 (s, 1H, NH, 11.05 (s, 1H, OH)].

Provenance & Evidence