Chloroform → HCID 12223711, compound

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Reaction Steps

8-Trifluoromethylphenothiazine-1-carboxylic acid (62.2 g., 0.20 mol.) was added to a stirred mixture of 300 ml. of chloroform and 300 ml. of phosphorus trichloride. The resulting brown suspension was cooled in an ice-bath while 50 ml. of dimethylformamide was added slowly until a reddish brown solution formed. After stirring the mixture for 4 hours at 25°, the chloroform and excess phosphorus trichloride were evaporated under reduced pressure. The resulting reddish brown solid residue was dissolved in 1500 ml. of boiling n-hexane. The hot, clear, reddish solution was decanted from a viscous, insoluble material and, on cooling, large red needles formed. The solid was collected by filtration and washed with hexane to give 8-trifluoromethylphenothiazine-1-carboxylic acid chloride, m.p. 124°-126°.

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