Sodium Nitrite → HCID 131714689, compound

Participants

Reaction Steps

Sodium nitrite fine powder (0.6 g ) was slowly added to a solution of 3-sec-butyl-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea (2.24 g, 5.64 mmol) in formic acid (10 ml) with thorough stirring at 0° to 5° C. spending 1 hour, and stirring was continued for further 2 hours at the same temperature. After confirmation by TLC that the reaction was finished, 20 g of an ion exchange resin (H+ form, registered trade mark: Amberlite IR-120) was added to the reaction mixture at 0° to 5° C., and the mixture was thoroughly stirred for 30 minutes. The ion exchange resin was filtered off, and the filtrate was vacuum-concentrated at 25° C. and crystallized from methanol and water, giving 1.41 g of 3-sec-butyl-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-1-nitrosourea; yield 58.7%, m.p. 68°-70° C., [α]D20 +67.5° (C 1.0, methanol).

Provenance & Evidence