Water → HCID 131714693, compound

Participants

Reaction Steps

2-Chloroethyl isocyanate (1.35 g) and silver carbonate (2.14 g) were added to a solution of n-butyl 6-(2-methyl-2-propenylamino)-6-deoxy-α-D-glucopyranoside hydrochloride (3.47 g, 10.6 mmol) in a mixture of water (25 ml) and acetonitrile (40 ml) at 0° to 5° C., and the mixture was heated under reflux on a water bath for 1 hour. Then, the reaction mixture was filtered while hot to remove the insoluble silver salt. The filtrate was vacuum-concentrated and crystallized from ethanol and water, giving 2.73 g of 3-(2-methyl-2-propenyl)-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea; yield 65.2%, m.p. 110°-112° C., [α]D20 +59.2° (C 1.0, methanol).

Provenance & Evidence