Triethylamine → Methylsulfamic acid 2-phenoxyethyl ester

HRID 327740Notes

Reaction equation

HRID 327740 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:11][NH:12][S:13](Cl)(=[O:15])=[O:14].C(N(CC)CC)C>C(#N)C>[O:1]([CH2:8][CH2:9][O:10][S:13](=[O:15])(=[O:14])[NH:12][CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31236PhenoxyethanolHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 53869191Methylsulfamic acid 2-phenoxyethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was prepared according to the procedure used in Example 112. Thus, a mixture of 14.8 g (0.1 mole) of 2-phenoxyethanol (Matheson, Coleman, and Bell), 15.6 g (0.12 mole) of methylsulfamoyl chloride and 12.3 g (0.12 mole) of triethylamine in 150 ml of acetonitrile gave a viscous oil that solidified upon standing. The solid was recrystallized from benzene-petroleum ether (30°-60° C.) to yield 15.4 g (67%) of shiny, white flakes, mp 66°-68° C.

Workup

  1. customThis compound was prepared
  2. customgave a viscous oil that
  3. customThe solid was recrystallized from benzene-petroleum ether (30°-60° C.)
  4. customto yield 15.4 g (67%) of shiny, white flakes, mp 66°-68° C.

Sources & evidence

ORD record
ord-c30c1087a6f44b6684745075d90ead88
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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