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

HRID 1987254Notes

Reaction equation

HRID 1987254 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

20% 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 was carried to 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 was carried to next step without further purification

Sources & evidence

ORD record
ord-7647928a52f5440bbf60c3f54d62ee39
Source dataset
uspto-grants-2009_06
Patent number
US07550506B2

Reaction notes

Loading…