O-Phenylenediamine → 3-(2-Thienyl)-1,2-dihydroquinoxalin-2-one

HRID 553451

反応式

HRID 553451 の反応式
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=O)[C:15](OCC)=[O:16]>CO>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[C:15](=[O:16])[NH:7][C:2]2[C:1]([N:8]=1)=[CH:6][CH:5]=[CH:4][CH:3]=2

参加物

4

反応物 2

HCID 7243O-PhenylenediamineHCID 77693Ethyl 2-thiopheneglyoxylate

生成物 1

HCID 7236983-(2-Thienyl)-1,2-dihydroquinoxalin-2-one収率 70.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of o-phenylenediamine (2.16 g, 20 mmol) and ethyl thiophene-2-glyoxylate (3.68 g, 20 mmol.) in anhydrous methanol (60 mL) was stirred at room temperature for 12 hours under nitrogen atmosphere. The precipitate formed during this time was collected and washed with methanol to give a crude yellow solid, which was recrystallized from ethanol to give pure 3(2-thienyl)quinoxalin-2(1 H)-one (3.2 g, 70%). 1 H NMR (400 MHz, DMSO-d6) δ 12.7 (s, 1 H), 8.39 (d, J=4.4 Hz, 1 H), 7.83 (d, J=5.2 Hz, 1 H), 7.77 (d, J=8.0 Hz, 1H), 7.50 (t, J=7.6 Hz, 1H), 7.35˜7.29 (m, 1 H), 7.22 (t, J=4.8 Hz, 1 H).

後処理

  1. customThe precipitate formed during this time
  2. customwas collected
  3. washwashed with methanol
  4. customto give a crude yellow solid, which
  5. customwas recrystallized from ethanol

出典と根拠

ORDレコード
ord-bf08d39f67eb41638511bdae3c1cb79a
出典データセット
uspto-grants-2011_11
特許番号
US08048862B2

関連ノート

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