Water → HCID 57756685, compound

HRID 227657Notes

Reaction equation

HRID 227657 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:8]([OH:10])[N:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br.O>CN(C)C=O.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:8]([O:10][CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[C:23]([F:22])([F:32])[F:33])[N:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 136088519HCID 136088519, compound

Product 1

HCID 57756685HCID 57756685, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-(acetylamino)-4-hydroxy-1,3-thiazole-5-carboxylate (6.04 g, 26.2 mmol) was dissolved in 100 mL of N,N-dimethylformamide with stirring. Potassium carbonate (3.98 g, 28.8 mmol) was added in a single portion. 2-Trifluoromethylbenzyl bromide (6.58 g, 27.5 mmol) in 20 mL of N,N-dimethylformamide was added via syringe. The reaction was stirred for 16 hours and poured into water and ethyl acetate. The layers were separated, and the organic layer was washed with brine. The combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash chromatography afforded 6.23 g (61%) of ethyl 2-(acetylamino)-4-({[2-(trifluoromethyl)-phenyl]methyl}oxy)-1,3-thiazole-5-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ 12.62 (s, 1H), 7.92 (m, 1H), 7.82-7.71 (m, 2H), 7.58 (m, 1H), 5.60 (s, 2H), 4.19 (q, J=7.2 Hz, 2H), 2.17 (s, 3H), 1.25 (t, J=7.2 Hz, 3H).

Workup

  1. stirringThe reaction was stirred for 16 hours
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. extractionThe combined aqueous layers were extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-c2bdb2c26a564102aebe61113b369d4c
Source dataset
uspto-grants-2009_07
Patent number
US07560568B2

Reaction notes

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