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

HRID 563049

Reaction equation

HRID 563049 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-d02b3c3fdfdd4b3691ca89641b90487c
Source dataset
uspto-grants-2011_11
Patent number
US08067455B2

Linked notes

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