Triethylamine → 2-(N,N-dimethylaminomethyl)thieno[2,3-b][1,5]benzoxazepin-4(5H)-one

HRID 1281887노트

반응식

HRID 1281887 반응식
O[CH2:2][C:3]1[S:17][C:6]2[O:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[CH:4]=1.[CH2:18]([N:20](CC)[CH2:21]C)C.CS(Cl)(=O)=O>C(Cl)Cl>[CH3:18][N:20]([CH2:2][C:3]1[S:17][C:6]2[O:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[CH:4]=1)[CH3:21]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 184221522-hydroxymethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one

생성물 1

HCID 184221852-(N,N-dimethylaminomethyl)thieno[2,3-b][1,5]benzoxazepin-4(5H)-one수율 45.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Hydroxymethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.0 g) was dissolved in methylene chloride (10 ml) and triethylamine (450 mg) and methanesulfonyl chloride (500 mg) were added. The mixture was stirred at room temperature for 15 minutes and the solvent was evaporated under reduced pressure. Thereto was added 2M dimethylamine/methanol and the mixture was stirred at room temperature for 14 hours. The solvent was evaporated under reduced pressure and chloroform was added to the residue. After washing with water, the aqueous layer was extracted twice with chloroform. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give 2-(N,N-dimethylaminomethyl)thieno[2,3-b][1,5]benzoxazepin-4(5H)-one (500 mg).

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. additionThereto was added 2M dimethylamine/methanol
  3. stirringthe mixture was stirred at room temperature for 14 hours
  4. customThe solvent was evaporated under reduced pressure and chloroform
  5. additionwas added to the residue
  6. washAfter washing with water
  7. extractionthe aqueous layer was extracted twice with chloroform
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-e6ac42fa18d74ec491969e8f7e8243f9
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455521B1

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