Thionyl Chloride → 4-(Chloromethyl)-2-(thiophen-2-yl)-1,3-thiazole

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[C:9]([CH2:11]O)[N:10]=1.S(Cl)([Cl:15])=O>>[Cl:15][CH2:11][C:9]1[N:10]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[S:7][CH:8]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 2776319[2-(2-Thienyl)-1,3-thiazol-4-YL]methanol

Product 1

HCID 7364964-(Chloromethyl)-2-(thiophen-2-yl)-1,3-thiazoleYield 65%

Procedure

In substantially the same manner as in Reference Example 73, 2-(2-thienyl)-4-thiazolylmethanol was allowed to react with thionylchloride to give 4-chloromethyl-2-(2-thienyl)thiazole. The yield was 65%. Recrystallization from ethyl acetate-hexane gave colorless needles, mp 54-55° C.

Sources & evidence

ORD record: ord-5a7fb9cf4746443198935858846d7d80
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211215B1

Reaction notes

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