4-(Trifluoromethyl)thiobenzamide → [5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]acetic acid ethyl ester

HRID 1869283

Reaction equation

HRID 1869283 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[S:11])[NH2:10])=[CH:5][CH:4]=1.[CH2:14]([O:16][C:17](=[O:24])[CH2:18][C:19](=O)[CH:20](Br)[CH3:21])[CH3:15]>C(O)C>[CH2:14]([O:16][C:17](=[O:24])[CH2:18][C:19]1[N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:4][CH:5]=2)[S:11][C:20]=1[CH3:21])[CH3:15]

Participants

4

Reactant 2

HCID 27348234-(Trifluoromethyl)thiobenzamideHCID 12780443Ethyl 4-bromo-3-oxopentanoate

Product 1

HCID 57986743[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]acetic acid ethyl esterYield 47.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 4-trifluoromethyl-benzene-thioamide (1.845 g, 9 mmol) in ethanol (15 mL, 200 proof) add ethyl-4-bromo-3-oxo-pentanoate (2.07 g, 9 mmol). Seal this solution warm the solution to 170° C. in a Personal Chemistry™ microwave oven and stir at this temperature for 20 min. Cool the resulting solution to room temperature, concentrate under reduced pressure and purify the residue by flash chromatography (elute with 30% ethyl acetate/10% dichloromethane in heptane) and obtain the title compound as a white solid (1.4 g). MS (ESI) m/z 330 (M+H); H1 NMR (CDCl3) δ1.87 (bs, 1H), 2.49 (s, 3H), 4.86 (s, 2H), 7.67 (d, J=8 Hz, 2H), 8.02 (d, J=8 Hz, 2H).

Workup

  1. customSeal this solution
  2. temperatureCool the resulting solution to room temperature
  3. concentrationconcentrate under reduced pressure
  4. custompurify the residue
  5. washby flash chromatography (elute with 30% ethyl acetate/10% dichloromethane in heptane)

Sources & evidence

ORD record
ord-06d1549a0fa74443bbd132a5937e5cac
Source dataset
uspto-grants-2009_12
Patent number
US07638539B2

Linked notes

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