Thionyl Chloride → 4-(Chloromethyl)-2-cyclopropylthiazole hydrochloride

HRID 1654212Notes

Reaction equation

HRID 1654212 reaction equation
[CH:1]1([C:4]2[S:5][CH:6]=[C:7]([CH2:9]O)[N:8]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl>[ClH:13].[CH:1]1([C:4]2[S:5][CH:6]=[C:7]([CH2:9][Cl:13])[N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20079576(2-Cyclopropylthiazol-4-yl)methanol

Product 1

HCID 187591664-(Chloromethyl)-2-cyclopropylthiazole hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In chloroform (10 ml) was dissolved 2-cyclopropyl-4-hydroxymethylthiazole (0.9 g), to which was added dropwise, under ice-cooling, thionyl chloride (0.68 ml), followed by stirring for 30 minutes at room temperature. Excess thionyl chloride was distilled off under reduced pressure. To the residue was added diethyl ether to yield 2-cyclopropyl-4-chloromethyl thiazole hydrochloride (1.1 g) as pale brown powder. m.p. 108°-110° C.

Workup

  1. additionto which was added dropwise, under ice-
  2. temperaturecooling
  3. distillationExcess thionyl chloride was distilled off under reduced pressure
  4. additionTo the residue was added diethyl ether

Sources & evidence

ORD record
ord-21dbd786b3184c6bb3ae790f12765813
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

Loading…