Thionyl Chloride → 2-(Chloromethyl)-4-methyl-1,3-thiazole hydrochloride

HRID 79469Notes

Reaction equation

HRID 79469 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7]O)[S:5][CH:6]=1.S(Cl)([Cl:11])=O>C1(C)C=CC=CC=1>[ClH:11].[Cl:11][CH2:7][C:4]1[S:5][CH:6]=[C:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 17750909(4-Methyl-1,3-thiazol-2-yl)methanol

Product 1

HCID 242788792-(Chloromethyl)-4-methyl-1,3-thiazole hydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (4-methylthiazol-2-yl)methanol (0.423 g, 3.27 mmol) in toluene (7 mL) was added thionyl chloride (0.478 mL, 6.55 mmol) dropwise. The mixture was heated to 65° C. and stirred for 1 hour. The mixture was concentrated under reduced pressure and the residue was triturated with ether. The solids were collected by filtration to afford 2-(chloromethyl)-4-methylthiazole hydrochloride (0.427 g, 71% yield) as pale yellow solids.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was triturated with ether
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-8b9be28aefdc4632932009fa98560e63
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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