Dimethyl Sulfoxide → HCID 54375901, compound

Participants

Reaction Steps

A mixture of N,N-diphenyl-6-amino-2-naphthaldehyde (4.8 g, 0.015 mol.), 2-methyl benzothiazole (3.0 g, 0.020 mol.), powdered potassium hydroxide (18.0 g, 0.32 mol.) and DMSO (30 ml) was stirred at room temperature for 1 hour, poured into water, and the solids which separated were collected by filtration. These solids were purified by column chromatography on alumina using 1:3 toluene-heptane as the eluent, to give 3.6 g. of product (53% yield) m.p. 181.1-184.8° C. Recrystallization from 1:1 toluene-ethyl acetate raised the m. p. to 201.8-203.8° C. Mass Spec: m/z 454, (M+). Analysis calculated for C31H22N2S: C, 81.92; H, 4.88; N, 6.16; S, 7.04. Found: C, 81.82; H, 4.93; N; 6.04, and S; 6.91.

Provenance & Evidence