Phosphorus sulfide (P2S5) → Ethyl 5-phenylthiazole-2-carboxylate

HRID 1397341Notes

Reaction equation

HRID 1397341 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].O=[C:16]([NH:22][CH2:23][C:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(Cl)(Cl)Cl>[C:25]1([C:24]2[S:2][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:22][CH:23]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 12830685Ethyl oxo((2-oxo-2-phenylethyl)amino)acetate

Product 1

HCID 12830686Ethyl 5-phenylthiazole-2-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

P2S5 (25.5 g, 114.7 mmol) was added to a solution of ethyl 2-oxo-2-((2-oxo-2-phenylethyl)amino)acetate (13.5 g, 57.39 mmol) in dry CHCl3 (150 mL), and the resulting reaction mixture was heated to reflux for 5 h. The reaction mixture was quenched with water and the organic product was extracted with CHCl3. The combined extracts were washed with H2O and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10-15% EtOAc in petroleum ether) to afford ethyl 5-phenylthiazole-2-carboxylate (10 g, yield 75%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.16 (s, 1H), 7.64-7.62 (m, 2H), 7.48-7.39 (m, 3H), 4.53-4.47 (q, J=7.0 Hz, 2H), 1.49-1.45 (t, J=7.2 Hz, 3H). MS (ESI) m/z: Calculated for C12H11NO2S: 233.05. found: 234.0 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 5 h
  4. customThe reaction mixture was quenched with water
  5. extractionthe organic product was extracted with CHCl3
  6. washThe combined extracts were washed with H2O and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10-15% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-214c34d712a149ccb81da76b4e7a1cdb
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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