Chlorosulfamic acid → 2-(3-Methoxyphenoxy)ethanol sulfamate

HRID 1613370Notes

Reaction equation

HRID 1613370 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[O:11][CH2:12][CH2:13][OH:14]>C(OCC)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[O:11][CH2:12][CH2:13][O:14][S:1](=[O:4])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 122988842-(3-Methoxyphenoxy)ethanol

Product 1

HCID 191086902-(3-Methoxyphenoxy)ethanol sulfamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared by procedures of Example 11 from sulfamoyl chloride and 2-(3-methoxyphenoxy)ethanol through the first evaporation step to give a brown, viscous, oily residue. The oil was dissolved in 300 ml of ethyl ether. The organic solution was washed with two 300 ml portions of water, dried over magnesium sulfate and the solvent evaporated under reduced pressure to give a viscous, oily residue for the second time. The oil was purified by chromatography using silica gel and methylene chloride-acetone in 90:1 ratio as eluting agent. Fractions containing the title compound were combined and solvents evaporated under reduced pressure to give a viscous oil which solidified on standing. The solid was recrystallized from ethyl-petroleum ether (bp range 30°-60° C.) to give the title compound as white solid, mp 78°-82° C., in 46% yield.

Workup

  1. customto give a brown, viscous, oily residue
  2. washThe organic solution was washed with two 300 ml portions of water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent evaporated under reduced pressure
  5. customto give a viscous, oily residue for the second time
  6. customThe oil was purified by chromatography
  7. washas eluting agent
  8. additionFractions containing the title compound
  9. customsolvents evaporated under reduced pressure
  10. customto give a viscous oil which
  11. customThe solid was recrystallized from ethyl-petroleum ether (bp range 30°-60° C.)

Sources & evidence

ORD record
ord-a7d8dba898424fd6a5f025e77d13a58c
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

Loading…