Phosphorus pentachloride → Butylsulfamyl chloride

HRID 1278573Notes

Reaction equation

HRID 1278573 reaction equation
[CH2:1]([NH:5][S:6](=[O:9])(=O)[OH:7])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)(Cl)[Cl:11]>C1C=CC=CC=1>[CH2:1]([NH:5][S:6]([Cl:11])(=[O:9])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 3628384butylsulfamic acid

Product 1

HCID 13544378Butylsulfamyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of n-butyl sulfamic acid (1.92 gm, 12.53 mmoles) and phosphorus pentachloride (2.61 gm, 12.53 mmoles) in benzene (20 mL) was warmed gently to initiate gas evolution. The reaction mixture was stirred at room temperature for 0.5 h., during which time a cloudy solution resulted. The cloudy solution was heated to reflux for 0.5 h., then was concentrated. The product n-butyl sulfamoyl chloride was isolated by vacuum distillation (120 C., 300 millitorr), 730 mg (liq.) (34%).

Workup

  1. temperaturewas warmed gently
  2. customresulted
  3. temperatureThe cloudy solution was heated
  4. temperatureto reflux for 0.5 h.
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-66518caf73794347ac44cfc98bb0a2db
Source dataset
uspto-grants-2002_09
Patent number
US06444678B1

Reaction notes

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