Thionyl Chloride → 2-Acetylthiomethyl-3-phenyl-propionyl chloride

HRID 1638355Notes

Reaction equation

HRID 1638355 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7](O)=[O:8])(=[O:3])[CH3:2].S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([Cl:19])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic Acid

Product 1

HCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolve 10 g (42 mmole) of 2-acetylthiomethyl-3-phenyl propionic acid and 10 g (84 mmole) of thionyl chloride in 50 ml of toluene. Stir for 10 hrs. under nitrogen and concentrate in vacuo. Dissolve the residue in 50 ml of toluene and again concentrate in vacuo. Repeat this step five times to obtain the product as a light brown oil.

Workup

  1. concentrationunder nitrogen and concentrate in vacuo
  2. dissolutionDissolve the residue in 50 ml of toluene
  3. concentrationagain concentrate in vacuo

Sources & evidence

ORD record
ord-856f4f1fab83410297a8ab8da646fb4e
Source dataset
uspto-grants-1989_11
Patent number
US04879309

Reaction notes

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