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

HRID 553451

반응식

HRID 553451 반응식
[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

참가 물질

4

반응물 2

HCID 7243O-PhenylenediamineHCID 77693Ethyl 2-thiopheneglyoxylate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bf08d39f67eb41638511bdae3c1cb79a
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048862B2

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