Oxalyl chloride → Methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate

HRID 625311Notes

Reaction equation

HRID 625311 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12].C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C)C=O>[Cl:21][C:11]([C:10]1[CH:9]=[C:8]([CH:16]=[CH:15][CH:14]=1)[CH2:7][S:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:17])=[O:12]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 434082543-((3-Methoxy-3-oxopropylthio)methyl)benzoic acid

Product 1

HCID 86705202Methyl 3-(3-(chlorocarbonyl)benzylthio)propanoateYield 91.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((3-methoxy-3-oxopropylthio)methyl)benzoic acid (61.6 mg, 0.24 mmol, 1.00 equiv) in dichloromethane (5 mL) was added dropwise oxalyl dichloride (121.76 mg, 0.96 mmol, 4.00 equiv) followed by a few drops of N,N-dimethylformamide. The resulting solution was heated to reflux for 30 min, then concentrated under vacuum to afford 60 mg (crude) of methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate as a yellow oil.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 30 min
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4863e2c5769441c9820a6d5e087d44ca
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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