p-Toluenesulfonic acid → 9-(2,2-Bis(4-chlorophenyl))ethoxy-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione

HRID 129456Notes

Reaction equation

HRID 129456 reaction equation
[OH:1][CH:2]1[C:14]2[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:25]O)=[CH:20][CH:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH:24]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)[CH2:25][O:1][CH:2]2[C:14]3[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]2=3)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 175334-Chloro-beta-(4-chlorophenyl)benzeneethanolHCID 190359859-Hydroxy-9H-indeno[1,2-b]pyrazine-2,3(1H,4H)-dione

Product 1

HCID 537438169-(2,2-Bis(4-chlorophenyl))ethoxy-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dioneYield 17.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 9-hydroxy-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione. 1H2O (0.50 g, 2.13 mmol) in acetic acid (30 ml), 2,2-bis(4-chlorophenyl)ethanol (2.84 g, 10.65 mmol) and p-toluensulfonic acid (20 mg) was refluxed for 21 hours. The reaction mixture was evaporated in vacuo to dryness, the residue was suspended in ethanol (40 ml) and the precipitate was filtered off and washed with ethanol and dried to give 0.39 g of the crude product, which was recrystallized from ethanol to yield 0.174 g (17.5%) of the title compound. M.p. 234°-237° C. 1H-NMR (DMSO-d6, δ): 3.68 (t, 1H), 4.0 (t, 1H), 4.27 (t, 1H), 5.23 (s, 1H), 7.1-7.5 (m, 12H), 11.98 (s, 1H), 12.25 (s, 1H).

Workup

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. filtrationthe precipitate was filtered off
  3. washwashed with ethanol
  4. customdried
  5. customto give 0.39 g of the crude product, which
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-86446b81494e404a84c039341f23ae1b
Source dataset
uspto-grants-1995_11
Patent number
US05468748

Reaction notes

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