Cyclamate → Cyclohexylsulfamyl chloride

HRID 2418985Notes

Reaction equation

HRID 2418985 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH:7]1([NH:13][S:14](=[O:17])(=O)[OH:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.P(Cl)(Cl)([Cl:20])=O>ClCCCl>[CH:7]1([NH:13][S:14]([Cl:20])(=[O:17])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 7533CyclamateHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachloride

Product 1

HCID 12914615Cyclohexylsulfamyl chlorideYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
95 °C

Procedure

54.2 parts of phosphorus pentachloride are added in portions to 89.6 parts of cyclohexylsulfamic acid, suspended in a mixture of 113 parts of 1,2-dichloroethane and 134 parts of phosphorus oxychloride, at 20° C, whilst stirring. The reaction mixture is then heated to 95° C in the course of 30 minutes and is stirred at from 95° to 98° C for 71/2 hours. After removing the solvent under reduced pressure distillation of the residue gives 94 parts (95% of theory) of cyclohexylsulfamic acid chloride of boiling point 103°-111° C/0.05 mm Hg (melting point 42°-44°).

Workup

  1. stirringis stirred at from 95° to 98° C for 71/2 hours
  2. customAfter removing the solvent
  3. distillationunder reduced pressure distillation of the residue

Sources & evidence

ORD record
ord-3fd424d7169b4b5db5368c9568576895
Source dataset
uspto-grants-1978_08
Patent number
US04104298

Reaction notes

Loading…