Phosphorus pentachloride → Butylsulfamyl chloride

HRID 1270431Notes

Reaction equation

HRID 1270431 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-5f7387c9933b4515ac3d944584f90208
Source dataset
uspto-grants-2007_04
Patent number
US07202258B2

Reaction notes

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