Methanol → Methyl 2-chloro-4-thiazolecarboxylate

HRID 70214Notes

Reaction equation

HRID 70214 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[N:10]=1.[CH3:14]O>>[Cl:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 218030262-Chloro-1,3-thiazole-4-carboxylic acid

Product 1

HCID 7213135Methyl 2-chloro-4-thiazolecarboxylateYield 65%

Procedure

Thionyl chloride (4.4 mL, 61 mmol) was added dropwise to a solution of 2-chlorothiazole-4-carboxylic acid (2.00 g, 12.2 mmol) in MeOH (40 mL) at 0° C., and the reaction mixture was allowed to warm to rt. After stirring overnight, the reaction mixture was concentrated under reduced pressure. The resulting solid was recrystallized from EtOH/H2O (1:1), yielding 1.40 g (65%) of the title compound as an orange solid. LC-MS: RT=6.17 min, [M+H]+=178.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe resulting solid was recrystallized from EtOH/H2O (1:1)

Sources & evidence

ORD record
ord-0a7d988ff41b4c7e91a5848120a68481
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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