Chloranil → HCID 178516979、化合物

HRID 926659ノート

反応式

HRID 926659 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:19]3[C:11](=[CH:12][C:13]4[CH:14]([C:21]5[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=5)[C:15](=[O:20])[NH:16][C:17]=4[CH:18]=3)[NH:10][C:9]2=[O:28])=[CH:4][CH:3]=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C(O)(=O)C>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([C:14]2[C:15](=[O:20])[NH:16][C:17]3[C:13]=2[CH:12]=[C:11]2[C:19](=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=4)[C:9](=[O:28])[NH:10]2)[CH:18]=3)=[CH:22][CH:23]=1

参加物

4

反応物 2

HCID 8371ChloranilHCID 666549393,7-Bis-(4-bromo-phenyl)-5,7-dihydro-1H,3H-pyrrolo[2,3-f]indole-2,6-dione

生成物 1

HCID 178516979HCID 178516979、化合物収率 63%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
50 °C

実験手順

3,7-Bis-(4-bromo-phenyl)-5,7-dihydro-1H,3H-pyrrolo[2,3-f]indole-2,6-dione (7.250 g, 14.55 mmol) (1.2) was dissolved into acetic acid (215 cm3), chloranil (7.157 g, 29.11 mmol) is added and the reaction mixture heated to 50° C. for 16 hours. After cooling down, the resulting precipitate is filtered and washed with acetic acid. The recovered solid is purified by trituration with nitrobenzene (120 cm3) at 200° C. followed by trituration with diethyl ether (100 cm3) to obtain the pure product (4.512 g, Yield: 63%). NMR (1H, 300 MHz, DMSO): δ 10.37 (br, 2H), 7.71 (d, J=8.7 Hz, 4H), 7.61 (d, J=8.7 Hz, 4H), 6.34 (s, 2H).

後処理

  1. additionis added
  2. temperatureAfter cooling down
  3. filtrationthe resulting precipitate is filtered
  4. washwashed with acetic acid
  5. customThe recovered solid is purified by trituration with nitrobenzene (120 cm3) at 200° C.

出典と根拠

ORDレコード
ord-31196ffcb01443799f52a990525057c1
出典データセット
uspto-grants-2016_03
特許番号
US09287504B2

反応ノート

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