Ethyl (chloroformyl)acetate → Ethyl 2-isopropylthiazole-5-carboxylate

HRID 471106Notes

Reaction equation

HRID 471106 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=[S:5])[NH2:4].Cl[CH:8]([CH:14]=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10]>CC(C)=O>[CH:2]([C:3]1[S:5][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][N:4]=1)([CH3:6])[CH3:1]

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 109095072-Methylpropanethioamide

Product 1

HCID 10608068Ethyl 2-isopropylthiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-methylpropanethioamide (3.3 g) and ethyl 2-chloro-3-oxopropanoate (4.82 g) in acetone (50 mL) was heated at reflux under nitrogen for 3 hours. The mixture was cooled to room temperature and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 12% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.6 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 3 hours
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by flash silica chromatography
  5. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-68fa01dd38a74f03b5b352baa2fdf58c
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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