Phenol → Phenylsulfamate

HRID 2305237Notes

Reaction equation

HRID 2305237 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 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of phenol (5.01 g, 53.2 mmol) in toluene (25 ml) was added a solution of chlorosulfonyl isocyanate (7.9 g, 55.9 mmol) in toluene (30 ml) at room temperature. The mixture was stirred at 120° C. for 14 hours. The solvent was removed in vacuo and the residue was added dropwise to water (75 ml). After stirring the resultant mixture at room temperature for 24 hours, the resulting precipitate was collected, washed with water, dissolved in EtOAc, washed with brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 1:1) to give sulfamic acid phenyl ester (5.52 g, 60%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was added dropwise to water (75 ml)
  3. stirringAfter stirring the resultant mixture at room temperature for 24 hours
  4. customthe resulting precipitate was collected
  5. washwashed with water
  6. dissolutiondissolved in EtOAc
  7. washwashed with brine successively
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-7a503d2b5aed400d8a8fdc4fb5e086eb
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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