Dimethylformamide → HCID 11096433, compound

HRID 467033Notes

Reaction equation

HRID 467033 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[CH:5][C:4]=1[S:13][CH3:14].C(Cl)(=O)C([Cl:18])=O.CN(C)C=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([Cl:18])=[O:11])=[CH:5][C:4]=1[S:13][CH3:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 19813064HCID 19813064, compound

Product 1

HCID 11096433HCID 11096433, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxy-3-(methylthio)phenylacetic acid (10.2 g, 47.3 mmol) in THF (300 mL) was added oxalyl chloride (6.6 g, 52 mmol, 1.1 equivalent) followed by a catalytic amount of N,N-dimethylformamide (DMF) (~0.5 mL). The reaction mixture was stirred at ambient temperature for 3 h and then concentrated under reduced pressure to give the title compound as a yellow oil. The product was used without purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3fc72c155f964d02a0f0b8466bde67ab
Source dataset
uspto-grants-1992_10
Patent number
US05158948

Reaction notes

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