Carbon Dioxide → 4-Chlorophenyl Sulfamate

HRID 1613390Notes

Reaction equation

HRID 1613390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[S:10]([N:13]=C=O)(=[O:12])=[O:11].O.C(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:10](=[O:12])(=[O:11])[NH2:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 46844-ChlorophenolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 101044834-Chlorophenyl SulfamateYield 10.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In one portion, 96 g (0.75 mole) of 4-chlorophenol was added to a stirred solution of 67.5 ml (0.75 mole) of chlorosulfonylisocyanate in 400 ml of toluene. The solution was heated at 100° C. for 16 hr and the solution chilled with an ice-acetone bath and water added dropwise until evolution of carbon dioxide ceased. The tan solid which precipitated from solution was collected and dried for 16 hr to yield 133.4 g. A 25 g portion was recrystallized from 100 ml of toluene to give 15.8 g of white solid, mp 103°-104° C.

Workup

  1. temperaturethe solution chilled with an ice-acetone bath
  2. customThe tan solid which precipitated from solution
  3. customwas collected
  4. customdried for 16 hr
  5. customto yield 133.4 g
  6. customA 25 g portion was recrystallized from 100 ml of toluene

Sources & evidence

ORD record
ord-dd9fca2966db4d258de740e417179a55
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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