Thionyl Chloride → 4-(N,N-diethylcarbamoyl)benzhydryl chloride

HRID 1038645

Reaction equation

HRID 1038645 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]([C:6]1[CH:19]=[CH:18][C:9]([CH:10](O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].S(Cl)([Cl:24])=O>ClCCl>[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]([C:6]1[CH:19]=[CH:18][C:9]([CH:10]([Cl:24])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 105409664-(N,N-diethylcarbamoyl)benzhydryl alcohol

Product 1

HCID 107330954-(N,N-diethylcarbamoyl)benzhydryl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(N,N-diethylcarbamoyl)benzhydryl alcohol (61.35 g, 216.5 mmol) was dissolved in 1500 mL of dichloromethane and 23.69 mL (324.8 mmol) of thionyl chloride was added dropwise. The reaction solution was stirred overnight at room temperature and the solvent was removed under vacuum. The crude product was redissolved in 800 mL of toluene and the solvent again was removed under vacuum to eliminate excess thionyl chloride, providing crude 4-(N,N-diethylcarbamoyl)benzhydryl chloride as a dark oil. Crude yield=100%.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe crude product was redissolved in 800 mL of toluene
  3. customthe solvent again was removed under vacuum

Sources & evidence

ORD record
ord-07fb7f0eb9c547a8986dcbd19795719b
Source dataset
uspto-grants-2013_10
Patent number
US08551998B2

Linked notes

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