Water → HCID 18917678, compound

Participants

Reaction Conditions

Reaction Steps

2-Ethyl-9-heptadecyl-4-(4-methylphenyl)-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (6 g) obtained in Example 18 was dissolved in dioxane (60 ml). Thereto were added water (60 ml) and sulfuric acid (2.9 ml) and the mixture was stirred at 80° C. for 2 hours. A solution of sodium nitrite (7.6 g) in water (25 ml) was gradually added dropwise and the mixture was stirred at 80° C. for 3 hours. After cooling, potassium carbonate was added thereto to make the reaction mixture alkaline. The mixture was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The oily substance obtained was crystallized from hexane to give 0.6 g of 5-ethyl-3-(4-methylbenzoyl)-2-(5-heptadecyl-3-hydroxymethyl-1,2,4-triazol-4-yl)thiophene as white crystals, melting point 68°-69° C.

Provenance & Evidence