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Sulfuric acid magnesium salt (1:1) → Ethyl 2-(methoxymethyl)-1,3-thiazole-4-carboxylate

HRID 1174127
Notes
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Reaction equation

HRID 1174127 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[S:6])[NH2:5].Br[CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].S([O-])([O-])(=O)=O.[Mg+2]>CC(C)=O>[CH3:1][O:2][CH2:3][C:4]1[S:6][CH:8]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66144Ethyl bromopyruvateHCID 203233692-Methoxyethanethioamide

Product 1

HCID 45117589Ethyl 2-(methoxymethyl)-1,3-thiazole-4-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes
Temperature
25 °C

Procedure

A solution containing the product from Example 6B (7 g, 66.6 mmol) in acetone (270 mL) was treated with ethyl bromopyruvate (8.4 mL, 66.6 mmol) and magnesium sulfate (7.9 g, 66.6 mmol), heated at reflux for 16 hours, cooled to 25° C., filtered and concentrated. The residue was chromatographed on silica gel eluting with chloroform to give the title compound (7.6 g, 57% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-c309c551cafd42dfad164da8f90a272b
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834043B2

Reaction notes

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