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

HRID 263913

反応式

HRID 263913 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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. 1 -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).

後処理

  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

出典と根拠

ORDレコード
ord-19fd8a0ddc62483d986376d860a55d3c
出典データセット
uspto-grants-1997_07
特許番号
US05646146

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