Water → 9H-Indeno[1,2-b]pyrazine-2,3,9(1H, 4H)-trione 9-ethylene dithioacetal

HRID 129454

反応式

HRID 129454 の反応式
[NH:1]1[C:6](=O)[C:5](=[O:8])[NH:4][C:3]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:15](=[O:16])[C:2]1=2.O.[CH2:18]([SH:21])[CH2:19][SH:20].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH2:18]1[S:21][C:6]2([C:5](=[O:8])[NH:4][C:3]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:15](=[O:16])[C:2]=3[NH:1]2)[S:20][CH2:19]1

参加物

6

反応物 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 190359779H-Indeno[1,2-b]pyrazine-2,3,9(1H,4H)-trione

生成物 1

HCID 867491119H-Indeno[1,2-b]pyrazine-2,3,9(1H, 4H)-trione 9-ethylene dithioacetal収率 83%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A suspension of 9H-indeno[1,2-b]pyrazine-2,3,9(1H, 4H)-trione. 0.9 H2O (2.0 g, 8.68 mmol) in toluene (50 ml), 1,2-ethanedithiol (2.19 ml, 26.04 mmol) and boron trifluoride etherate (1.07 ml, 8.68 mmol) was refluxed for 20 hours. The reaction mixture was cooled to room temperature, and the precipitate was filtered off and washed with toluene, ethanol-water (2:1) and ethanol. The crude material (2.40 g) was recrystallized from DMF-water to give 2.09 g (83%) of the title compound. M.p. >300° C. 1H-NMR (DMSO-d6, δ): 3.68 (m, 2H), 3.91 (m, 2H), 7.2 (t, 1H), 7.3 (t, 1H), 7.51 (d, 1H), 7.59 (d, 1H), 12.05 (s, 1H), 12.38 (s, 1H).

後処理

  1. filtrationthe precipitate was filtered off
  2. washwashed with toluene, ethanol-water (2:1) and ethanol
  3. customThe crude material (2.40 g) was recrystallized from DMF-water

出典と根拠

ORDレコード
ord-e3791f7b9e7e4eae98cbd9f962e98b24
出典データセット
uspto-grants-1995_11
特許番号
US05468748

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