N,N-Dimethylaniline → 2,6-Di(propan-2-yl)phenyl carbonochloridate

HRID 1436941Notes

Reaction equation

HRID 1436941 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH:11]([CH3:13])[CH3:12])[C:9]=1[OH:10])[CH3:3].[C:14](Cl)([Cl:16])=[O:15].CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH:11]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:2]([CH3:1])[CH3:3])[C:9]=1[O:10][C:14]([Cl:16])=[O:15])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 4943PropofolHCID 6371Phosgene

Product 1

HCID 2716192,6-Di(propan-2-yl)phenyl carbonochloridate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cooled (0° C.) solution of propofol (20.0 g, 112 mmol) in toluene (40 mL) was added phosgene (82 mL, 20% in toluene) under a nitrogen atmosphere. The reaction mixture was stirred for 5 min, and then N,N-dimethylaniline (15 mL, 118 mmol) was added dropwise. The mixture was allowed to warm to room temperature slowly and stirred for 14 h. The suspended mixture was then filtered. The filtrate was collected and the solvent was removed in vacuo. The remaining crude product (9) was carried to the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.18-7.29 (m, 3H), 3.00-3.07 (m, 2H), 1.25-1.27 (d, J=6.8 Hz, 12H).

Workup

  1. stirringstirred for 14 h
  2. filtrationThe suspended mixture was then filtered
  3. customThe filtrate was collected
  4. customthe solvent was removed in vacuo
  5. customThe remaining crude product (9) was carried to the next step without further purification

Sources & evidence

ORD record
ord-3f7d03ea21814291a0899b86e0fe2076
Source dataset
uspto-grants-2009_11
Patent number
US07619110B2

Reaction notes

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