Chlorosulfamic acid → 2-(4-Bromophenyl)ethyl sulfamate

HRID 414604Notes

Reaction equation

HRID 414604 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[S:13](Cl)(=[O:16])(=[O:15])[NH2:14]>CN(C=O)C>[S:13](=[O:16])(=[O:15])([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1)[NH2:14]

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 144420712-(4-Bromophenyl)ethyl sulfamateYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 2.95 g (0.015 mole) of 4-bromophenethyl alcohol in 10 ml DMF was added dropwise to a suspension of sodium hydride 0.90 g, 60% in oil; 0.065 mole) in 35 ml DMF at 0°-5° C. The suspension was stirred for 20 min under argon after which sulfamoyl chloride (2.09 g, 0.018 mole) was added portionwise at 0°-5° C. After stirring for 20 min, the resultant suspension was poured into ice and extracted twice with Et2O. The combined organic phases were washed with saturated brine, dried over potassium carbonate and concentrated in vacuo to a white solid which was recrystallized in EtOAc/hexane to give 2.40 g (59%) of the title compound as a white solid, mf 109°-110° C.

Workup

  1. customat 0°-5° C
  2. additionwas added portionwise at 0°-5° C
  3. extractionextracted twice with Et2O
  4. washThe combined organic phases were washed with saturated brine
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated in vacuo to a white solid which
  7. customwas recrystallized in EtOAc/hexane

Sources & evidence

ORD record
ord-90502743931444b2b0f4940741d0ea4d
Source dataset
uspto-grants-1988_12
Patent number
US04792569

Reaction notes

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