Benzoyl chloride → N-[2-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]ethyl]benzamide

HRID 748312노트

반응식

HRID 748312 반응식
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]2[S:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21](=[O:23])[N:22]=2)[CH:12]=1.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C(=O)C.O>[O:23]=[C:21]1[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[S:18][C:17]([C:13]2[CH:12]=[C:11]([CH2:10][CH2:9][NH:8][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:16]=[CH:15][N:14]=2)=[N:22]1

참가 물질

7

반응물 4

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 684561462-[4-(2-Aminoethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

생성물 1

HCID 59750348N-[2-[2-(4-Oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]ethyl]benzamide수율 36.6%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
60 °C

실험 절차

2-[4-(2-Aminoethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (0.50 g, 1.2 mmol) was dissolved in N,N-dimethylacetamide (10 ml), and benzoyl chloride (0.36 g, 2.6 mmol) and potassium carbonate (0.17 g, 1.2 mmol) were added thereto. The reaction mixture was stirred at 60° C. for 5 hrs, combined with ethyl acetate and water. The organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with methanol-ethyl acetate (1:20, v/v) were collected, concentrated and recrystallized from hexane-chloroform to give the titled compound (0.17 g, 36%) as white crystals.

후처리

  1. washThe organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washThe fractions eluted with methanol-ethyl acetate (1:20
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from hexane-chloroform

출처 및 근거

ORD 기록
ord-21501fa3ef4e46939bc2849279616bc4
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399759B2

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