Chlorosulfonyl isocyanate → HCID 54144007, compound

HRID 2289687Notes

Reaction equation

HRID 2289687 reaction equation
C(=O)=[N:2][S:3](Cl)(=[O:5])=[O:4].[CH:8]([C:11]1[CH:16]=[C:15]([S:17][C:18]#[N:19])[CH:14]=[C:13]([CH:20]([CH3:22])[CH3:21])[C:12]=1[OH:23])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1>[CH:8]([C:11]1[CH:16]=[C:15]([S:17][C:18]#[N:19])[CH:14]=[C:13]([CH:20]([CH3:22])[CH3:21])[C:12]=1[O:23][S:3](=[O:4])(=[O:5])[NH2:2])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 186988422,6-Diisopropyl-4-thiocyanato-phenol

Product 1

HCID 54144007HCID 54144007, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Chlorosulfonyl isocyanate (1.02 mL, 11.7 mmol) was added to a warm solution of 2,6-diisopropyl-4-thiocyanato-phenol (2.5 g, 10.6 mmol) in 150 mL toluene. The resulting solution was heated to reflux for 6 hours and then cooled to room temperature and stirred overnight. The reaction was concentrated in vacuo and the residue was quenched with ice water and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 1.75 g of sulfamic acid 2,6-diisopropyl-4-thiocyanato-phenyl ester as a white solid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 6 hours
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe residue was quenched with ice water
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-be747cbf3dbc489b862d16dee8ed0ec3
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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