Dimethylformamide → HCID 14390807, compound

HRID 346186Notes

Reaction equation

HRID 346186 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-6e0628a880364e728e5ea0214e1e1dcc
Source dataset
uspto-grants-1991_10
Patent number
US05061710

Reaction notes

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