Dimethylformamide → cis-3-(Acetylthio)propenoyl chloride

HRID 374276Notes

Reaction equation

HRID 374276 reaction equation
[C:1]([S:4]/[CH:5]=[CH:6]\[C:7]([OH:9])=O)(=[O:3])[CH3:2].CN(C)C=O.C(Cl)(=O)C([Cl:18])=O>C1(C)C=CC=CC=1>[C:1]([S:4]/[CH:5]=[CH:6]\[C:7]([Cl:18])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86746379cis-3-(Acetylthio)propenoic acid

Product 1

HCID 86746380cis-3-(Acetylthio)propenoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2.8 g (0.0162 mol) of cis-3-(acetylthio)propenoic acid and 0.1 ml of N,N-dimethylformamide in 50 ml of toluene under nitrogen was added 2.84 ml (0.0325 mol) of oxalyl chloride. After 3 h the solvents were removed to give cis-3-(acetylthio)propenoyl chloride. This crude product was used in the next step without any further purification.

Workup

  1. customAfter 3 h the solvents were removed

Sources & evidence

ORD record
ord-d342777803884175a753a6f611084d0c
Source dataset
uspto-grants-1992_11
Patent number
US05166390

Reaction notes

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