Sodium hydride → HCID 14726791, compound

Participants

Reaction Steps

2-(3- Chloro-2-methylpropyl)naphthol1,8-cd]isothiazole 1,1-dioxide may be prepared in the following manner: the experiment is carried out as in Example 56 for the preparation of 2-(3-bromo-2-hydroxypropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide, starting with naphtho[1,8-cd]isothiazole 1,1-dioxide (10.3 g) in dimethylformamide (125 cc), sodium hydride (2.4 g) in a 50% dispersion in vaseline oil, and 1-bromo-3-chloro-2-methylpropane (5.9 cc). After purification by flash-chromatography on a silica column, under a current of argon at medium pressure (0.5-1.5 bar) with a mixture of dichloromethane and cyclohexane (80-20 vol) as eluant, 2-(3-chloro-2-methylpropyl)naphtho[1,8-cd]isothiazole 1,1-dioxide (10.4 g) is obtained, in the form of a green oil, which is used in the crude state in the subsequent syntheses.

Provenance & Evidence