4-(Dimethylamino)Benzaldehyde → HCID 178482697, compound

Participants

Reaction Steps

A solution of 0.40 g (1.28 mmoles) of 4-(4-dimethylaminophenyl)-5-(4-fluorophenyl)-2-mercaptoimidazole, a Formula (IV) compound, [obtained by treatment of the corresponding Formula (VIII) compound (prepared from 4-dimethylaminobenzaldehyde and 4-fluorobenzaldehyde as described by Ide et al., in "Organic Reactions"; John Wiley and Sons, (1948) Chapter 5) with thiourea in DMF by the method described in Bender et al., J. Med. Chem., 28, 1169 (1985) (therein designated as the general method for preparation of 4,5-diarylimidazole-2-thiones)] in 15 ml of dry DMF was treated with 0.061 g (1.28 mmoles) of a 50% sodium hydride dispersion. 0.18 g (1.28 mmoles) of 1-bromo-2-chloroethane was added after 0.5 hours stirring at ambient temperature. After an additional 12 hours stirring, 0.18 g (1.28 mmoles) of powdered potassium carbonate was added, and the mixture heated to 150° C. for 2 hours. The solvent was removed in vacuo and the residue extracted with chloroform. The solution was washed with water, dried over MgSO4 and concentrated in vacuo. Column chromatography on silica afforded two isomers eluting with 10% and 20% CH3CN in CH2Cl2. Evaporation of the solvents followed by recrystallization from methanol gave 5-(4-dimethylaminophenyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole, mp 163°-164.5° C., (TLC, silica, 10% CH3CN in CH2Cl2, Rf 0.17) and 6-(4-dimethylaminophenyl)-5-(4-fluorophenyl)-2,3-dihydroimid azo[2,1-b]thiazole, mp 195°-201° C., (TLC, silica, 10% CH2CN in CH2Cl2, Rf 0.3).

Provenance & Evidence