Potassium Carbonate → ethyl 4-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

HRID 560740Notes

Reaction equation

HRID 560740 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[C:16](=[O:17])[NH:15][N:14]=[CH:13]2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>CC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[C:16](=[O:17])[N:15]([CH2:30][C:29]3[CH:28]=[CH:27][C:26]([C:25]([F:24])([F:34])[F:35])=[CH:33][CH:32]=3)[N:14]=[CH:13]2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Product 1

HCID 58031587ethyl 4-methyl-2-(5-oxo-1-(4-(trifluoromethyl)benzyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate (0.17 g, 0.68 mmol) and potassium carbonate (0.14 g, 1.03 mmol) in acetone (10 mL) was added 4-(trifluoromethyl)benzyl bromide (0.21 g, 0.89 mmol). The reaction mixture was heated to reflux for 3 hours. The solvent was removed in vacuo and the residue was washed with water and hexanes to afford the title compound in 60% yield (0.17 g): 1H NMR (300 MHz, CDCl3) δ 8.29 (s, 1H), 7.61 (d, J=8.3 Hz, 2H), 7.50 (d, J=8.3 Hz, 2H), 5.07 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 2.67 (s, 3H), 1.35 (t, J=7.1 Hz, 3H); MS (ES+) m/z 413.2 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with water and hexanes

Sources & evidence

ORD record
ord-44b7ac0966dd42bfb14a77ee8b235a84
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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