Boron trifluoride etherate → 9H-Indeno[1,2-b]pyrazine-3,9(4H)-dione 9-ethylene dithioacetal

HRID 263910Notes

Reaction equation

HRID 263910 reaction equation
[N:1]1[C:2]2[C:14](=[O:15])[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:3]=2[NH:4][C:5](=O)[CH:6]=1.[CH2:16]([SH:19])[CH2:17][SH:18].B(F)(F)F.CCOCC>C1C=CC=CC=1>[CH2:16]1[S:19][C:5]2([NH:4][C:3]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[C:14](=[O:15])[C:2]=3[N:1]=[CH:6]2)[S:18][CH2:17]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 190359769H-Indeno[1,2-b]pyrazine-3,9(4H)-dione

Product 1

HCID 867491109H-Indeno[1,2-b]pyrazine-3,9(4H)-dione 9-ethylene dithioacetalYield 64%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 9H-indeno[1,2-b]pyrazine-3,9(4H)-dione (0.50 g, 2.52 mmol) in benzene (10 ml), 1,2-ethanedithiol (0.63 ml, 7.56 mmol) and boron trifluoride etherate (0.31 ml, 2.52 mmol) was refluxed for 23 hours. The reaction mixture was cooled to room temperature, and the precipitate was filtered off and washed with benzene and water and dried. The crude material (0.64 g) was recrystallized twice from ethanol to give 0.44 g (64%) of the title compound. M.p. 284°-290° C. 1 -NMR (DMSO-d6, δ): 3.75-3.94 (m, 4H), 7.46-7.57 (m, 2H), 7.8 (m, 2H), 7.95 (s, 1H), 12.6 (s, 1H).

Workup

  1. temperaturewas refluxed for 23 hours
  2. filtrationthe precipitate was filtered off
  3. washwashed with benzene and water
  4. customdried
  5. customThe crude material (0.64 g) was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-48c01f9bfca7409cb30856e8cf26f9a9
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Reaction notes

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