Cyclamate → Cyclohexylsulfamyl chloride

HRID 640031

Reaction equation

HRID 640031 reaction equation
[CH:1]1([NH:7][S:8](=[O:11])(=O)[OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)(Cl)[Cl:13]>C1(C)C=CC=CC=1>[CH:1]1([NH:7][S:8]([Cl:13])(=[O:11])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7533CyclamateHCID 24819Phosphorus pentachloride

Product 1

HCID 12914615Cyclohexylsulfamyl chlorideYield 82.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a solution of N-cyclohexylsulfamic acid (50 g, 279 mmol) and PCl5 (58.1 g, 279 mmol) in 150 mL of toluene is very gently warmed up to 100° C. and maintained at that temperature for 1 hour. Distillation of the solution yields N-cyclohexylsulfamoyl chloride as a colorless solid (45.5 g, 82%).

Workup

  1. temperaturemaintained at that temperature for 1 hour
  2. distillationDistillation of the solution

Sources & evidence

ORD record
ord-ade2508b1acf415787124703329b534f
Source dataset
uspto-grants-2010_04
Patent number
US07691929B2

Linked notes

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