Dimethylformamide → HCID 14390807, compound

HRID 257542Notes

Reaction equation

HRID 257542 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[C:7](O)=[O:8])(=[O:3])[CH3:2].CN(C=O)C.S(Cl)([Cl:30])=O>C1(C)C=CC=CC=1>[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[C:7]([Cl:30])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 10380931HCID 10380931, compound

Product 1

HCID 14390807HCID 14390807, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneCatalystHCID 1140TolueneSolvent

Procedure

To 3-acetylthio-2-(4-phenylbenzyl)propionic acid (3.39 g, 10.8 mmole) in toluene (25 ml) add 1% DMF in toluene (2 drops) and thionyl chloride (1.2 ml, 1.65 g, 13.8 mmoles) and stir the resulting solution at room temperature for 18 hours. Concentrate the reaction mixture in vacuo, dissolve the residue in toluene (100 ml) and concentrate the solution in vacuo to give the title compound, a light brown oil (3.37 g).

Workup

  1. concentrationConcentrate the reaction mixture in vacuo
  2. dissolutiondissolve the residue in toluene (100 ml)
  3. concentrationconcentrate the solution in vacuo

Sources & evidence

ORD record
ord-7a35fa9b53bd4d51aadfa06b9a1f5c2d
Source dataset
uspto-grants-1993_11
Patent number
US05262436

Reaction notes

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