Dicyclohexylcarbodiimide → N-[4-(3-Bromopropoxy)phenyl]-9,10-dihydro-9-oxo-4-acridinecarboxamide

HRID 1451644ノート

反応式

HRID 1451644 の反応式
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16](O)=[O:17])[C:10]=2[NH:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.ON1C2C=CC=CC=2N=N1.[Br:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[Br:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:16]([C:11]2[C:10]3[NH:9][C:8]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:2](=[O:1])[C:15]=3[CH:14]=[CH:13][CH:12]=2)=[O:17])=[CH:36][CH:35]=1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 35607584-Carboxy-9-acridanoneHCID 199745634-(3-Bromopropoxy)aniline

生成物 1

HCID 15299131N-[4-(3-Bromopropoxy)phenyl]-9,10-dihydro-9-oxo-4-acridinecarboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 9,10-dihydro-9-oxo-4-acridinecarboxylic acid (1.5 g) and 1-hydroxybenzotriazole (1.1 g) in DMF (50 ml) was stirred at room temperature for 10 min. The product of part (ii) above (1.5 g) was then added followed by dicyclohexylcarbodiimide (1.3 g), and the mixture was stirred at room temperature for 16 h and then filtered. The filtrate was concentrated in vacuo, treated with water and extracted with dichloromethane. The combined, dried organic extracts were concentrated to give the title compound (0.5 g) which was recrystallised from acetonitrile, MP 126°.

後処理

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiontreated with water
  5. extractionextracted with dichloromethane
  6. concentrationdried organic extracts were concentrated

出典と根拠

ORDレコード
ord-87016f6b3580417eabca14c9e3f9c9a1
出典データセット
uspto-grants-1997_02
特許番号
US05604237

反応ノート

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