Water → HCID 18917588, compound

Participants

Reaction Conditions

Reaction Steps

2-Ethyl-4-(4-methoxylphenyl)-9-undecyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (8.0 g) obtained in Example 16 was suspended in water (200 ml). Thereto was added sulfuric acid (7.6 ml) and the mixture was stirred at 80° C. for 2 hours. Thereto was gradually added dropwise a solution of sodium nitrite (7.6 g) in water (25 ml) 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 to give 4.4 g of 5-ethyl-3-(4-methoxybenzoyl)-2-(3-hydroxymethyl-5-undecyl-1,2,4-triazol-4-yl)thiophene as an oily substance.

Provenance & Evidence