Triethylamine → 3-Phenoxy-1,2-propanediol bissulfamate

To the above sulfamoyl chloride solution in acetonitrile was added dropwise with stirring a solution of 8.4 g (0.05 mole) of 3-phenoxy-1,2-propanediol (95% purity obtained from Aldrich Chem. Co., Inc.) and 20.2 g (0.2 mole) of triethylamine in 50 ml of acetonitrile at such a rate that the temperature did not exceed 12° C. over a 45 min period. The cooling bath was removed and the mixture was stirred for 2 hr and treated with 100 ml of ethyl acetate and 50 ml of water. The mixture was vigorously stirred for 5 min and the layers were separated. The organic layer was washed with 50 ml of water and 100 ml of salt brine, dried over sodium sulfate and concentrated to give a gum as residue. The gum was purified by column chromatography on 350 g of silica gel. Fractions eluted with 15% acetone in methylene chloride were combined and concentrated to give a clear gum as residue. The gum was triturated with petroleum ether (b.p. 30°-60° C.) to give crystalline solid. The solid was collected by filtration and recrystallized from benzene-acetonitrile to yield 4.2 g (26% yield) of white solid title compound, mp 116°-118° C.

1. customThe cooling bath was removed
2. additiontreated with 100 ml of ethyl acetate and 50 ml of water
3. stirringThe mixture was vigorously stirred for 5 min
4. customthe layers were separated
5. washThe organic layer was washed with 50 ml of water and 100 ml of salt brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customto give a gum as residue
9. customThe gum was purified by column chromatography on 350 g of silica gel
10. washFractions eluted with 15% acetone in methylene chloride
11. concentrationconcentrated
12. customto give a clear gum as residue
13. customThe gum was triturated with petroleum ether (b.p. 30°-60° C.)
14. customto give crystalline solid
15. filtrationThe solid was collected by filtration
16. customrecrystallized from benzene-acetonitrile

ORD-Eintrag

ord-b9c81e9390394da5888ee64452b6444a

Quelldatensatz

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05273993