Acetyl chloride → N-(3,4-Dimethoxy-6-methylphenanthren-9-yl)acetamide

HRID 746003ノート

反応式

HRID 746003 の反応式
C(N(C(C)C)C(C)C)C.[NH2:10][C:11]1[C:12]2[C:17]([C:18]3[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=3[CH:24]=1)=[CH:16][C:15]([CH3:29])=[CH:14][CH:13]=2.[C:30](Cl)(=[O:32])[CH3:31]>C(Cl)Cl>[C:30]([NH:10][C:11]1[C:12]2[C:17]([C:18]3[C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=3[CH:24]=1)=[CH:16][C:15]([CH3:29])=[CH:14][CH:13]=2)(=[O:32])[CH3:31]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 137729823,4-Dimethoxy-6-methylphenanthren-9-amine

生成物 1

HCID 13772983N-(3,4-Dimethoxy-6-methylphenanthren-9-yl)acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

105.7 ml (0.750M) of N-ethyl-N,N-diisopropyl-amine are added to a solution of 100.2 g (0.375M) of 9-amino-3,4-dimethoxy-6-methyl-phenanthrene in 1000 ml methylene chloride. To the resulting mixture is added dropwise over 30 minutes a solution of 34.5 ml (0.450M) of acetyl chloride in 250 ml methylene chloride. During the addition, the temperature of the reaction mixture is maintained at 20° by cooling with ice. The reaction mixture is stirred for 2 hours at room temperature and extracted with methylene chloride. The organic phases are washed with ice cooled 2N hydrochloric acid, water and 2N sodium bicarbonate, dried over sodium sulfate and evaporated, to give the title compound. M.pt. 190°-192° after crystallization from acetone/ether.

後処理

  1. additionDuring the addition
  2. temperaturethe temperature of the reaction mixture is maintained at 20°
  3. temperatureby cooling with ice
  4. extractionextracted with methylene chloride
  5. washThe organic phases are washed with ice
  6. temperaturecooled 2N hydrochloric acid, water and 2N sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. customevaporated

出典と根拠

ORDレコード
ord-f7719ade5240409bbef9d8b9598211f3
出典データセット
uspto-grants-1986_07
特許番号
US04602032

反応ノート

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