Dimethylformamide → 3-Phenylprop-2-enoyl chloride

HRID 1086373Notes

Reaction equation

HRID 1086373 reaction equation
CS[C:3]1[CH:13]=[CH:12][C:11](CCCC2C=CC=CC=2)=[CH:10][C:4]=1[CH:5]=[CH:6][C:7](O)=[O:8].CN(C=O)C.C(Cl)(=O)C([Cl:31])=O>C(Cl)Cl>[C:7]([Cl:31])(=[O:8])[CH:6]=[CH:5][C:4]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 54153260HCID 54153260, compound

Product 1

HCID 660233-Phenylprop-2-enoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To dry methylene chloride (32 ml) there is added 2-methylthio-5-(3-phenylpropyl)cinnamic acid (1.0 g, 3.2 mmol). To this mixture is added DMF (0.25 ml, 3.2 mmol) and the reaction mixture cooled in an ice bath. Oxalyl chloride (.61 ml, 7.04 mmol) is slowly added dropwise and the resulting mixture stirred at room temperature for 2 hours to afford 2-methylthio-5-3-phenylpropyl)cinnamic acid chloride in solution.

Workup

  1. temperaturethe reaction mixture cooled in an ice bath

Sources & evidence

ORD record
ord-5820eedd9fdd4ed0a432780fc98f0298
Source dataset
uspto-grants-1991_07
Patent number
US05028629

Reaction notes

Loading…