N-methoxy-N-methyl-2-phenyl-1,3-thiazole-5-carboxamide → 1-(2-Phenyl-thiazol-5-yl)-propan-1-one

HRID 396395

Reaction equation

HRID 396395 reaction equation
CON(C)[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][CH:7]=1)=[O:5].[CH2:18]([Mg]Br)[CH3:19]>O1CCCC1>[C:11]1([C:9]2[S:10][C:6]([C:4](=[O:5])[CH2:18][CH3:19])=[CH:7][N:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 9921229N-methoxy-N-methyl-2-phenyl-1,3-thiazole-5-carboxamideHCID 178418443HCID 178418443, compound

Product 1

HCID 98559161-(2-Phenyl-thiazol-5-yl)-propan-1-oneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.32 g (1.3 mmol) of the above-prepared 2-phenyl-thiazole-5-carboxylic acid methoxy-methyl-amide in tetrahydrofuran at room temperature was added 0.34 g (2.6 mmol) of 1M ethyl magnesium bromide in tetrahydrofuran. The reaction mixture was allowed to stir for one hour. The reaction was quenched with aqueous ammonium chloride and partitioned with ethyl acetate. The organic phase was washed once with aqueous ammonium chloride, once with water, once with brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using 1:19 ethyl acetate:hexanes to give 0.26 g of the title compound (93%). 1H NMR (500 MHz, CDCl3) δ 8.36 (s, 1H) 8.0 (m, 2H) 7.49 (m, 3H) 2.98 (q, 2H) 1.27 (t, 3H).

Workup

  1. customThe reaction was quenched with aqueous ammonium chloride
  2. custompartitioned with ethyl acetate
  3. washThe organic phase was washed once with aqueous ammonium chloride, once with water, once with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel using 1:19 ethyl acetate

Sources & evidence

ORD record
ord-72e022f3a8f44bb9a816509c3d54aa4f
Source dataset
uspto-grants-2003_08
Patent number
US06608087B1

Linked notes

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