Chlorosulfamic acid → HCID 14442070, compound

HRID 414603Notes

Reaction equation

HRID 414603 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][OH:8].[H-].[Na+].[S:16](Cl)(=[O:19])(=[O:18])[NH2:17]>CN(C=O)C>[S:16](=[O:19])(=[O:18])([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1)[NH2:17]

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 819113,4-Dimethoxyphenethyl alcohol

Product 1

HCID 14442070HCID 14442070, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 5.0 g (0.027 mole) of 3,4-dimethoxy phenethyl alcohol in 12 ml DMF was added dropwise to a suspension of sodium hydride (1.20 g, 60% in oil; 0.09 mole) in 40 ml DMF at 0°-5° C. The suspension was stirred for 20 min under argon after which sulfamoyl chloride (3.54 g, 0.03 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 0.95 g (13%) of the title compound as a solid, mp 106°-108° C. Both 13C and 1H NMR in CDCl3 confirmed the structure.

Workup

  1. additionwas added portionwise at 0°-5° C
  2. additionwas poured into ice
  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-eb76cc9cde9e43409f9050795b5ca585
Source dataset
uspto-grants-1988_12
Patent number
US04792569

Reaction notes

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