Phosgene → Cyclohexylsulfamyl chloride

HRID 866773Notes

Reaction equation

HRID 866773 reaction equation
CN(C)C([Cl:5])=O.C(Cl)(Cl)=O.[CH:11]1([NH:17][S:18](=[O:21])(=O)[OH:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>ClCCCl>[CH:11]1([NH:17][S:18]([Cl:5])(=[O:21])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6371Phosgene3×HCID 6598Dimethylcarbamoyl ChlorideHCID 7533Cyclamate

Product 1

HCID 12914615Cyclohexylsulfamyl chlorideYield 58%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
83 °C

Procedure

A solution of 15 parts of dimethylcarbamic acid chloride in 310 parts of 1,2-dichloroethane is saturated with 30 parts of phosgene at 25° C and 89.5 parts of cyclohexylsulfamic acid are then added. The reaction mixture is heated to 83° C whilst continuing to introduce phosgene. In total, 330 parts of phosgene are introduced in the course of 13 hours. After removing the solvent and the dimethylcarbamic acid chloride under reduced pressure, the residue is distilled, and 57 parts (58% of theory) of cyclohexylsulfamic acid chloride of boiling point 208°-127° C/0.1 mm Hg and melting point 42°-44° C are obtained.

Workup

  1. customAfter removing the solvent
  2. distillationthe dimethylcarbamic acid chloride under reduced pressure, the residue is distilled

Sources & evidence

ORD record
ord-bd6bdfb9311641829d0d03b08693b735
Source dataset
uspto-grants-1978_07
Patent number
US04101571

Reaction notes

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