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

HRID 443122Notes

Reaction equation

HRID 443122 reaction equation
[NH2:1][C:2]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)=[S:3].Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O>[N:4]1([C:2]2[S:3][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:1]=2)[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66144Ethyl bromopyruvateHCID 23935444-Morpholinecarbothioamide

Product 1

HCID 15053544Ethyl 2-(morpholin-4-yl)-1,3-thiazole-4-carboxylateYield 55.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.85 g (12.7 mmol) of 4-((amino)thiocarbonyl)morpholine, 1.59 ml (12.7 mmol) of ethyl bromopyruvate, and excess MgSO4 in 50 ml of acetone was heated at reflux for 2 h. The resulting mixture was allowed to cool, filtered, and concentrated in vacuo. The residue was taken up in chloroform, washed with aqueous NaHCO3, dried over Na2SO4, and concentrated. Silica gel chromatography using 1% methanol in chloroform provided 1.7 g (55%) of the desired compound, Rf 0.70 (ethyl acetate). Mass spectrum: (M+H)+ =243.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washwashed with aqueous NaHCO3
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-90b941ba99434f869fd82e6e691a9dc7
Source dataset
uspto-grants-1999_04
Patent number
US05892052

Reaction notes

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