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

HRID 585108

반응식

HRID 585108 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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 IM 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).

후처리

  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

출처 및 근거

ORD 기록
ord-311e5aa8c64547f9b5a3f1f2301ba48e
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930116B2

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