Thionyl Chloride → 5-Chloromethyl-2-(4-chlorophenyl)thiazole

HRID 1849975Notes

Reaction equation

HRID 1849975 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:13]O)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>ClCCl>[Cl:17][CH2:13][C:10]1[S:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59562416[2-(4-Chlorophenyl)thiazol-5-yl]methanol

Product 1

HCID 595624855-Chloromethyl-2-(4-chlorophenyl)thiazoleYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of [2-(4-chlorophenyl)thiazol-5-yl]methanol (3.24 g, 14.3 mmol) in dichloromethane (40 ml) is added dropwise the thionyl chloride (1.3 ml, 18 mmol) at room temperature under nitrogen. The reaction mixture is stirred at room temperature for 4 hours. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 5-chloromethyl-2-(4-chlorophenyl)thiazole (3.24 g)

Workup

  1. additionSilica gel is added to the crude
  2. customreaction mixture
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-0b240d2eaf9645ea991853f99463f79f
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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