Phenol → Phenylsulfamate

HRID 1271272Notes

Reaction equation

HRID 1271272 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:9]([N:12]=C=O)(=[O:11])=[O:10]>C1(C)C=CC=CC=1>[C:1]1([O:7][S:9](=[O:11])(=[O:10])[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 11030308PhenylsulfamateYield 70.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of 4.98 g of phenol in 9 ml of toluene, a solution of 7.49 g of chlorosulfonyl isocyanate in 5 ml of toluene was added dropwise at an inner temperature of 45° C. or lower. After the completion of dropwise addition, the mixture was heated in an oil bath at 110° C. and continuously stirred for 12 hours. The reaction solution was ice-cooled and the insoluble matter was removed by filtration, and then the filtrate was heated in an oil bath at 40° C. While stirring vigorously, 1.2 ml of water was slowly added dropwise. The reaction solution was ice-cooled and the deposited crystal was collected by filtration, washed with toluene and then dried under reduced pressure to obtain 6.46 g of the desired compound as a colorless crystal having a melting point of 78 to 80° C.

Workup

  1. additionAfter the completion of dropwise addition
  2. temperaturecooled
  3. customthe insoluble matter was removed by filtration
  4. temperaturethe filtrate was heated in an oil bath at 40° C
  5. stirringWhile stirring vigorously
  6. addition1.2 ml of water was slowly added dropwise
  7. temperaturecooled
  8. filtrationthe deposited crystal was collected by filtration
  9. washwashed with toluene
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-1563a2354d9d4481aa595b89a25f68be
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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