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

HRID 52714Notes

Reaction equation

HRID 52714 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[C:4]([NH2:6])=[S:5])[CH3:2].Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13].[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O>[CH2:1]([N:3]([C:4]1[S:5][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:6]=1)[CH2:7][CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66144Ethyl bromopyruvateHCID 854389Diethylthiourea

Product 1

HCID 12966399Ethyl 2-(diethylamino)-1,3-thiazole-4-carboxylateYield 140.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 0.972 g (7.36 mmol) of N,N-diethylthiourea and 1.02 ml (8.1 mmol) of ethyl bromopyruvate in 25 ml of acetone was treated with excess solid MgSO4 and heated at reflux for 1 h. The resulting mixture was filtered, and concentrated in vacuo. Silica gel chromatography using CHCl3 provided 2.36 g (38%) of the desired compound as an oil. Mass spectrum: (M+H)+ =229.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. filtrationThe resulting mixture was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f65c23a8c4e475c9b50b4eb895d1480
Source dataset
uspto-grants-1997_04
Patent number
US05616720

Reaction notes

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