O-Phenylenediamine → 2-(1H-Pyrrol-2-yl)-1H-benzimidazole

HRID 6431

반응식

HRID 6431 반응식
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[NH:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](O)=O>C(=O)(O)[O-].[Na+]>[NH:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=1

참가 물질

4

반응물 2

HCID 7243O-PhenylenediamineHCID 12473Pyrrole-2-Carboxylic Acid

생성물 1

HCID 6394192-(1H-Pyrrol-2-yl)-1H-benzimidazole수율 27.3%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

반응 조건

온도
80 °C

실험 절차

A mixture of 1.08 g (10 mmol) of o-phenylenediamine and 20 g of polyophosphate esters was heated gently at 80° C. and was added portionwise 1.11 g (10 mmol) of pyrrole-2-carboxylic acid. After the mixture was stirred at 100° C. for 30 minutes, it was poured into a saturated solution of sodium bicarbonate (500 mL) and stirred until polyphosphate esters was decomposed. It was then extracted with two 400 mL portions of ethyl acetate. the separated organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product. After purification by column chromatography on silica gel with 30% ethyl acetate in hexane, the desired product, 2-(pyrrol-2-yl)benzimidazole (0.50 g, 25%) was obtained as a pale yellow solid, m.p. 250° C.; 1H-NMR (Acetone-d6) 6.25-6.27 (m, 1H, ArH), 6.90-6.92 (m, 1H, ArH), 7.02-7.03 (m, 1H, ArH), 7.14-7.19 (m, 2H, 2xArH), 7.52 (bs, 2H, 2xArH).

후처리

  1. extractionIt was then extracted with two 400 mL portions of ethyl acetate
  2. dry with materialthe separated organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customAfter purification by column chromatography on silica gel with 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-f133d8b34fb84de6ae33d093fc5b41e4
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248782

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