Ethanol → Ethyl 3-(4-phenylthiazol-2-yl)propanoate

HRID 1397332Notes

Reaction equation

HRID 1397332 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][C:12](=[S:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].[CH3:20]CO>>[C:5]1([C:3]2[N:11]=[C:12]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:20])=[O:16])[S:19][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6259Phenacyl bromideHCID 18333020Methyl 4-amino-4-thioxobutanoate

Product 1

HCID 67325597Ethyl 3-(4-phenylthiazol-2-yl)propanoateYield 40%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo acetophenone (2.1 g, 10.55 mmol) and methyl 4-amino-4-thioxobutanoate (1.6 g, 10.86 mmol) in EtOH (15 mL) was heated to 80° C. for 3 h. Reaction mixture was cooled to room temperature and solvent was evaporated under reduced pressure. The product was extracted with EtOAc and the organic layer was washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford ethyl 3-(4-phenylthiazol-2-yl)propanoate (1.1 g, yield 40%) as a white solid, which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.90-7.87 (m, 2H), 7.44-7.39 (m, 2H), 7.35-7.30 (m, 2H), 4.22-4.15 (q, J=7.2 Hz, 2H), 3.41-3.36 (t, J=7.5 Hz, 2H), 2.94-2.89 (t, J=7.3 Hz, 2H), 1.30-1.25 (t, J=7.1 Hz, 3H). MS (ESI) m/z: Calculated for C14H15NO2S: 261.08. found: 262.2 (M+H)+.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customsolvent was evaporated under reduced pressure
  4. extractionThe product was extracted with EtOAc
  5. washthe organic layer was washed with H2O and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-127a4d1b04454c45bdbc1465da020fdf
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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