Phosphorus pentachloride → Phenylsulfamoyl chloride

HRID 857904Notes

Reaction equation

HRID 857904 reaction equation
[C:1]1([NH:7][S:8](=[O:11])(=O)[O-:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:14]>C1(C)C=CC=CC=1>[C:1]1([NH:7][S:8]([Cl:14])(=[O:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 2366421315790-84-8

Product 1

HCID 11564615Phenylsulfamoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of sodium phenylsulfamate (200 mg, prepared according to the procedure of Audrieth and Sveda, J. Org. Chem., 1944, 9, 89) in dry toluene (5 mL), under a blanket of nitrogen, was treated with PCl5 (267 mg). After stirring at 80° C. for 20 hours the reaction mixture was allowed to cool to room temperature and then evaporated to give the title compound (100 mg) as a brown oil, which was used without further purification.

Workup

  1. customprepared
  2. temperatureto cool to room temperature
  3. customevaporated

Sources & evidence

ORD record
ord-120162fd3b824b68adbd44f1958095bd
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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