Ethyl bromopyruvate → Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

HRID 2203116Notes

Reaction equation

HRID 2203116 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C:5](=[S:7])[NH2:6])[CH3:2].Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CCO>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C:5]1[S:7][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 27947342,2-Diethoxythioacetamide

Product 1

HCID 16220290Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,2-diethoxyethanethioamide (2 g), ethyl bromopyruvate (1.61 ml), MS-4A (2 g) and EtOH (15 ml) was heated under reflux for 1 h. The mixture was concentrated, and the residue was diluted with AcOEt. The mixture was washed with water and brine successively, dried with MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (2.5 g) as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. concentrationThe mixture was concentrated
  4. additionthe residue was diluted with AcOEt
  5. washThe mixture was washed with water and brine successively
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-17e13e06abf94b878f1361a06775c20f
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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