Sodium Carbonate → Ethyl 1,3-thiazole-2-carboxylate

HRID 1660736Notes

Reaction equation

HRID 1660736 reaction equation
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:14]([O:13][C:11]([C:3]1[S:4][CH:5]=[CH:6][N:7]=1)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 5884532-Trimethylsilylthiazole

Product 1

HCID 13032471Ethyl 1,3-thiazole-2-carboxylateYield 85,247%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 2-trimethylsilylthiazole (135 g, 858 1 mmol) in toluene (1350 mL) add a solution of ethyl chloroformate (98.4 mL, 1.03 mol) in toluene (1350 mL) over 15 min. Stir the reaction at 22° C. for 2 h. Add the solution over aqueous sodium carbonate 25% (wt/wt) (5 L) and stir for 30 min. Separate the organic layer and re-extract the aqueous layer with methylene chloride (2×1 L). Combine the organic layers and evaporate the solvent to provide the title compound (134 g, 99%). ES/MS m/z 158 (M+1)+.

Workup

  1. customthe reaction at 22° C. for 2 h
  2. stirringstir for 30 min
  3. customSeparate the organic layer
  4. extractionre-extract the aqueous layer with methylene chloride (2×1 L)
  5. customCombine the organic layers and evaporate the solvent

Sources & evidence

ORD record
ord-c26c4e0a81ed40ca9dbe3486108af4a8
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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