Magnesium Carbonate → 5-Thiazolecarboxylic acid, 4-methyl-, ethyl ester

HRID 1374930Notes

Reaction equation

HRID 1374930 reaction equation
[CH:1]([NH2:3])=[S:2].Cl[CH:5]([C:11]([CH3:13])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)([O-])[O-].[Mg+2]>O1CCOCC1>[CH3:13][C:11]1[N:3]=[CH:1][S:2][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 11029Magnesium CarbonateHCID 11858Ethyl 2-chloroacetoacetateHCID 3005587Methanethioamide

Product 1

HCID 2986105-Thiazolecarboxylic acid, 4-methyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Thioformamide (7.5 g, 122.72 mmol), ethyl 2-chloroacetoacetate (16.4 g, 99.52 mmol) and magnesium carbonate (20 g, 237.22 mmoL) were taken dioxane (100 mL) and heated at 110° C. for 4 hrs. The reaction mixture was cooled to room temperature and filtered to remove magnesium carbonate. The solvent was evaporated to dryness and the residue was taken in ether (200 mL) and washed successively with 0.5 M NaOH solution (200 mL×2) and saturated brine solution (100 mL) and dried over Na2SO4. It was filtered and evaporated to give 4-methyl-5-(ethoxycarbonyl)thiazole as an oil which was purified by silica gel column chromatography using hexanes:EtOAc (8:2, v/v) as a eluent; yield: 3.28 g (17%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto remove magnesium carbonate
  4. customThe solvent was evaporated to dryness
  5. washwashed successively with 0.5 M NaOH solution (200 mL×2) and saturated brine solution (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationIt was filtered
  8. customevaporated

Sources & evidence

ORD record
ord-91210069d59f45c1b0edaa997cdbb412
Source dataset
uspto-grants-2007_01
Patent number
US07166625B2

Reaction notes

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