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

HRID 129454노트

반응식

HRID 129454 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e3791f7b9e7e4eae98cbd9f962e98b24
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468748

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