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

HRID 2036177Notes

Reaction equation

HRID 2036177 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-a0040c3c157e4e6583cec23df4a85320
Source dataset
uspto-grants-2013_11
Patent number
US08575169B2

Reaction notes

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