Triethylamine → Sulfamic acid, 3-phenylpropyl ester

HRID 1613745Notes

Reaction equation

HRID 1613745 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[C:6]1([CH2:12][CH2:13][CH2:14][OH:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>C(#N)C>[S:1]([O:15][CH2:14][CH2:13][CH2:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 31234Benzenepropanol

Product 1

HCID 11447235Sulfamic acid, 3-phenylpropyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was obtained using the following procedure: The sulfamoyl chloride in solution prepared in (a) was reacted as in Example 12 with 16.4 g (0.118 mole) of 3-phenyl-1-propanol (98%) using 46.4 g (0.459 mole) of triethylamine in 100 ml of additional acetonitrile followed by using the extracting, washing and concentration procedures of Example 12 through the first evaporation. The viscous, oily residue was partitioned between water and ethyl ether (300 ml each). The organic layer was separated and washed with four 200 ml portions of water, the aqueous wash being finally neutral to pH paper. The organic layer was dried over magnesium sulfate and the solvent was evaporated under reduced pressure to give 19.5 g of a light-yellow, viscous oil which solidified on standing. The solid was recrystallized using ethyl ether and petroleum ether (bp range 30°-60° C.) to give 12.1 g (48%) of title compound as white solid, mp 56.5°-58° C.

Workup

  1. washwashing
  2. concentrationconcentration procedures of Example 12
  3. customthrough the first evaporation
  4. customThe viscous, oily residue was partitioned between water and ethyl ether (300 ml each)
  5. customThe organic layer was separated
  6. washwashed with four 200 ml portions of water
  7. washthe aqueous wash
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customto give 19.5 g of a light-yellow, viscous oil which
  11. customThe solid was recrystallized
  12. customethyl ether and petroleum ether (bp range 30°-60° C.)

Sources & evidence

ORD record
ord-388f71625ed04f068dd4ac8ed677be98
Source dataset
uspto-grants-1993_03
Patent number
US05194446

Reaction notes

Loading…