Magnesium Carbonate → 5-Thiazolecarboxylic acid, 4-methyl-, ethyl ester
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered
- customto remove magnesium carbonate
- customThe solvent was evaporated to dryness
- washwashed successively with 0.5 M NaOH solution (200 mL×2) and saturated brine solution (100 mL)
- dry with materialdried over Na2SO4
- filtrationIt was filtered
- customevaporated
Sources & evidence
- ORD record
- ord-0ffc17e79d55422f801ad1375d5dfd20
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432254B2
Reaction notes
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