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

HRID 6431

反応式

HRID 6431 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f133d8b34fb84de6ae33d093fc5b41e4
出典データセット
uspto-grants-1993_09
特許番号
US05248782

関連ノート

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