Thionyl Chloride → Ethyl 2-chloro-4-(chlorocarbonyl)-1,3-thiazole-5-carboxylate

Reaction equation

[Cl:1][C:2]1[S:3][C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([C:7](O)=[O:8])[N:6]=1.S(Cl)([Cl:17])=O>>[Cl:1][C:2]1[S:3][C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([C:7]([Cl:17])=[O:8])[N:6]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 592083472-Chloro-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid2×

Product 1

HCID 59208443Ethyl 2-chloro-4-(chlorocarbonyl)-1,3-thiazole-5-carboxylate

Procedure

2-Chloro-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid (Intermediate 7, 1 g, 4.24 mmol) was dissolved in thionyl chloride (5 mL) and refluxed for two hours. It was then concentrated to give the desired product (light brown oil, 1 g). NMR (CDCl3): 1.37 (t, 3H), 4.39 (q, 2H).

Workup

temperaturerefluxed for two hours
concentrationIt was then concentrated

Sources & evidence

ORD record: ord-687a1ecbf229478b948212be5b9c9ea0
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

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