N,N-Dimethylaniline → HCID 22272761, compound

HRID 1064846Notes

Reaction equation

HRID 1064846 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([OH:11])=[CH:4][C:3]=1[CH:12]([CH3:14])[CH3:13].CN(C)C1C=CC=CC=1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>ClCCl.O>[CH:12]([C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([CH:8]([CH3:9])[CH3:10])[C:2]=1[NH:1][C:25](=[O:26])[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 15891Phenyl chloroformateHCID 22272644HCID 22272644, compound

Product 1

HCID 22272761HCID 22272761, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-3,5-diisopropylphenol (1.02 g, 5.27 mmol) in dichloromethane (10 ml) was added N,N-dimethylaniline (770 mg, 6.34 mmol), then a solution of phenyl chloroformate (910 mg, 5.81 mmol) in dichloromethane (2 ml) was dropped thereinto with ice-cooling and stirring, and the mixture was stirred for 30 minutes. The reaction solution was diluted with water and extracted with dichloromethane. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 34 g, developing solvent; hexane:acetone=5:1) to provide 1.27 g (77%) of phenyl N-(2,6-diisopropyl-4-hydroxyphenyl)carbamate as colorless oil.

Workup

  1. temperaturewith ice-cooling
  2. stirringthe mixture was stirred for 30 minutes
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (silica gel 34 g, developing solvent; hexane:acetone=5:1)

Sources & evidence

ORD record
ord-9462416162cb43189483b74e3bb26b8d
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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