Water → HCID 54193382, compound

Participants

Reaction Steps

2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(2-amino-1,2-dicyanoethenylimino)methyl]-2H-1,2,3-triazole (8 g) (prepared as in Example 1) was dissolved in methanol (50 ml) and tetrahydrofuran (75 ml) and then sodium borohydride (0.76 g) was added portionwise. This mixture was stirred for 20 minutes at room temperature and then poured into water to give a brown solid. This was purified by flash column chromatography to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(2-amino-1,2-dicyanoethenylamino)methyl]-2H-1,2,3-triazole, m.p. 191°-192°. A mixture of this compound (1.8 g), nicotinamide (0.6 g), N-chlorosuccinimide (0.6 g) and dimethylformamide was heated at 65°-70° for 10 minutes. The mixture was poured into water and extracted with diethyl ether. Conventional work-up and purification by flash column chromatography gave 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-(4,5-dicyano-4-imidazolin-2-yl)-2H-1,2,3-triazole, m.p. 21920 -220° (dec). (Compound 10).

Provenance & Evidence