Chlorosulfonyl isocyanate → 2,6-Bis(1-methylethyl)-4-nitrophenyl sulfamate

HRID 2289673Notes

Reaction equation

HRID 2289673 reaction equation
C(=O)=[N:2][S:3](Cl)(=[O:5])=[O:4].[CH3:8][CH:9]([C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[C:13]([CH:20]([CH3:22])[CH3:21])[C:12]=1[OH:23])[CH3:10]>C1(C)C=CC=CC=1>[S:3](=[O:4])(=[O:5])([O:23][C:12]1[C:13]([CH:20]([CH3:21])[CH3:22])=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:11]=1[CH:9]([CH3:10])[CH3:8])[NH2:2]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 106806032,6-Diisopropyl-4-nitrophenol

Product 1

HCID 186988452,6-Bis(1-methylethyl)-4-nitrophenyl sulfamateYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Chlorosulfonyl isocyanate (7.2 mL, 82.6 mmol) was added slowly to a warm solution of 2,6-bis(1-methylethyl)-4-nitrophenol (17.57 g, 78.7 mmol) in 400 mL toluene. The resulting solution was heated to reflux for 6 hours and then cooled to room temperature and concentrated to give a brown oil. Quenched with 200 g ice and extracted with 4×500 mL dichloromethane. The organic solution was dried over MgSO4, filtered, and concentrated to give a tan solid. Recrystallization from dichloromethane gave 14.18 g (60%) of the title compound as an off-white solid; mp 163-167° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 6 hours
  3. concentrationconcentrated
  4. customto give a brown oil
  5. customQuenched with 200 g ice
  6. extractionextracted with 4×500 mL dichloromethane
  7. dry with materialThe organic solution was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a tan solid
  11. customRecrystallization from dichloromethane

Sources & evidence

ORD record
ord-b2525d5950614c7c8d08f494e1e14117
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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