Diethyl Ether → 58484-09-6

To a solution of 300 mg of 1-(2-chloroethyl)-3-(β-D-galactopyranosyl)urea in 2 ml of 99% formic acid was slowly added 150 mg of sodium nitrite in an icebath under stirring. The mixture was stirred for 1 hour under ice-cooling to complete the nitrosation. The reaction mixture was admixed with 50 ml of ethyl ether to deposit an oily substance. The ethyl ether phase was separated from the oily substance by decantation. The operation of adding ethyl ether to and separating the ethyl ether phase from the oily substance by decantation was repeated three times, using 50 ml, 20 ml and 20 ml of the ether, respectively. Thereafter, the oily substance was taken up into 30 ml of methyl alcohol, and the resultant solution was admixed with 3 ml of Amberlite IR-120 (H+ form). The admixture was filtered to remove cation-exchange resin, and the filtrate was concentrated under a reduced pressure, depositing crystals of the titled compound. Yield 210 mg (63.6%). mp. 145° C. (decomposition with foaming). [α]D21.0 +13.0° (c 0.5, H2O).

1. stirringThe mixture was stirred for 1 hour under ice-
2. temperaturecooling
3. customThe ethyl ether phase was separated from the oily substance by decantation
4. customThe operation of adding ethyl ether to and separating the ethyl ether phase from the oily substance by decantation
5. filtrationThe admixture was filtered
6. customto remove cation-exchange resin
7. concentrationthe filtrate was concentrated under a reduced pressure
8. custom[α]D21.0 +13.0° (c 0.5, H2O)

ORD record

ord-e531d8ccc1e94997b660a265ea46ac47

Source dataset

uspto-grants-1979_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04180655