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

HRID 1991395Notes

Reaction equation

HRID 1991395 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH3:5][CH:6]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH:15]([CH3:17])[CH3:16])[C:13]=1[OH:14])[CH3:7].CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH:15]([C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:6]([CH3:7])[CH3:5])[C:13]=1[O:14][C:1]([Cl:4])=[O:2])([CH3:17])[CH3:16]

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 1140TolueneSolvent2×

Procedure

A 20% solution of phosgene in toluene (139 mL, 0.269 mol) was added to a stirring solution of propofol (40 g, 0.225 mmol) in toluene (80.0 mL) under a nitrogen atmosphere at 0° C. N,N-Dimethylaniline (34.0 mL, 0.269 mmol) was added dropwise over 15 minutes. The reaction mixture was allowed to warm to room temperature slowly and stirred for 14 h. The reaction mixture was filtered through Celite and the solvent was removed in vacuo. The crude product (2) was carried to the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.29-7.25 (m, 1H), 7.19-7.17 (m, 2H), 3.04-3.01 (m, 2H), 1.25 (d, J=7.2 Hz, 12H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed in vacuo
  3. customThe crude product (2) was carried to the next step without further purification

Sources & evidence

ORD record
ord-aacc2413b5544b04b4ae3569df9d62b2
Source dataset
uspto-grants-2010_01
Patent number
US07645792B2

Reaction notes

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