Chlorosulfonyl isocyanate → HCID 18698847, compound

HRID 2289683Notes

Reaction equation

HRID 2289683 reaction equation
C(=O)=[N:2][S:3](Cl)(=[O:5])=[O:4].[C:8]([Si:12]([CH3:28])([CH3:27])[O:13][C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([OH:23])=[C:16]([CH:24]([CH3:26])[CH3:25])[CH:15]=1)([CH3:11])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1>[S:3](=[O:4])(=[O:5])([O:23][C:17]1[C:16]([CH:24]([CH3:26])[CH3:25])=[CH:15][C:14]([O:13][Si:12]([C:8]([CH3:9])([CH3:11])[CH3:10])([CH3:27])[CH3:28])=[CH:19][C:18]=1[CH:20]([CH3:22])[CH3:21])[NH2:2]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 186988374-(Tert-butyl-dimethyl-silanyloxy)-2,6-diisopropylphenol

Product 1

HCID 18698847HCID 18698847, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Chlorosulfonyl isocyanate (3.43 mL, 39.4 mmol) was added to a warm solution of 4-(tert-butyl-dimethyl-silanyloxy)-2,6-diisopropylphenol (11.59 g, 37.6 mmol) in 400 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 an orange oil. Chromatography on silica gel gave 6.06 g of 4-(tert-butyl-dimethyl-silanyloxy)-2,6-diisopropylphenyl sulfamate as an orange oil.

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
  9. customto give an orange oil

Sources & evidence

ORD record
ord-affc43a758644be1830c83964d674abc
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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