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

HRID 263911Notes

Reaction equation

HRID 263911 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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
  4. customto give 2.09 g (83%) of the title, compound

Sources & evidence

ORD record
ord-c67660fa133f4f72b92c003fc573e3aa
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Reaction notes

Loading…