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

HRID 1281887ノート

反応式

HRID 1281887 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e6ac42fa18d74ec491969e8f7e8243f9
出典データセット
uspto-grants-2002_09
特許番号
US06455521B1

反応ノート

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