Dimethylformamide → 3-Benzylmercapto-4-chlorocarbonyl benzaldehyde

HRID 2072305Notes

Reaction equation

HRID 2072305 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[C:17]([OH:19])=O)[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:22])=O.CN(C)C=O>C(Cl)Cl>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[C:17]([Cl:22])=[O:19])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 539168353-Benzylmercapto-4-carboxy benzaldehyde

Product 1

HCID 536823133-Benzylmercapto-4-chlorocarbonyl benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 23.2 g of 3-benzylmercapto-4-carboxy benzaldehyde in 250 ml of methylene chloride is added 15 ml of thionyl chloride and 0.5 ml of dimethylformamide. The reaction mixture is refluxed for 6-7 hours, then evaporated to dryness. Crystallization from 100 ml of ether yielded 27.0 g of 3-benzylmercapto-4-chlorocarbonyl benzaldehyde (a).

Workup

  1. temperatureThe reaction mixture is refluxed for 6-7 hours
  2. customevaporated to dryness
  3. customCrystallization from 100 ml of ether

Sources & evidence

ORD record
ord-44e2cdc2638042c2b7194d606af3c913
Source dataset
uspto-grants-1977_09
Patent number
US04051148

Reaction notes

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