1,2-苯二胺 → 2-(1H-Pyrrol-2-yl)-1H-benzimidazole

HRID 6431

反应方程式

HRID 6431 反应方程式
[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

参与物

4

反应物 2

HCID 72431,2-苯二胺HCID 12473吡咯-2-羧酸

产物 1

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

试剂、催化剂与溶剂 1

HCID 516892碳酸氢钠溶剂

反应条件

温度
80 °C

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-f133d8b34fb84de6ae33d093fc5b41e4
来源数据集
uspto-grants-1993_09
专利号
US05248782

关联笔记

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