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

HRID 926758Notes

Reaction equation

HRID 926758 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

Into a 50-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-((3-methoxy-3-oxopropylthio)methyl)benzoic acid (61.6 mg, 0.24 mmol, 1.00 equiv) in dichloromethane (5 mL). This was followed by dropwise addition of oxalyl dichloride (121.76 mg, 0.96 mmol, 4.00 equiv) with stirring at room temperature. Then a few drops of N,N-dimethylformamide were added as catalyst. The resulting solution was heated to reflux for 30 min. The resulting mixture was concentrated under vacuum to yield 60 mg (crude) of methyl 3-(3-(chlorocarbonyl)benzylthio)propanoate as yellow oil. The crude was used directly in the next step.

Workup

  1. customInto a 50-mL round bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 30 min
  5. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-9a742a4f1ea04b14b229392e3663fff7
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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