2-Phenylethanol → HCID 11816502, compound

HRID 327660Notes

Reaction equation

HRID 327660 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[CH:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][OH:14])=[CH:8][CH:7]=1>C(#N)C>[S:1]([O:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=1)(=[O:4])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 60542-PhenylethanolHCID 24499Chlorosulfamic acid

Product 1

HCID 11816502HCID 11816502, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The title compound was obtained using the following procedure: The sulfamoyl chloride in acetonitrile solution prepared in (a) was reacted as in Example 12 with 12.2 g (0.1 mole) of β-phenethyl alcohol using 40.4 g (0.4 mole) triethylamine in 100 ml additional acetonitrile followed by using extracting, washing and concentration procedures of Example 12 through the first evaporation. The crude oily residue was purified by chromatography (10×80 cm glass column; 700 g silica gel; eluents methylene chloride followed by 10:1 methylene chloride/acetone). Fractions containing the title compound were combined and solvents evaporated under reduced pressure to give 13.6 g (68% yield) of title compound as light-yellow oil.

Workup

  1. extractionby using extracting
  2. washwashing
  3. concentrationconcentration procedures of Example 12
  4. customthrough the first evaporation
  5. customThe crude oily residue was purified by chromatography (10×80 cm glass column; 700 g silica gel; eluents methylene chloride followed by 10:1 methylene chloride/acetone)
  6. additionFractions containing the title compound
  7. customsolvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-8369efcfcc9442d2a05ddde9b7f8ff68
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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