O-Phenylenediamine → 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol

HRID 1776876ノート

反応式

HRID 1776876 の反応式
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19]C)=[C:14]([CH:18]=1)[C:15](O)=O.[OH-].[K+]>>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=[C:15]1[C:14]1[CH:18]=[C:10]([Cl:9])[CH:11]=[CH:12][C:13]=1[OH:19]

参加物

4

反応物 3

HCID 7243O-PhenylenediamineHCID 14797Potassium HydroxideHCID 769705-Chloro-o-anisic acid

生成物 1

HCID 35112112-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol収率 27%

反応条件

温度
200 °C

実験手順

A mixture of benzene-1,2-diamine (500 mg, 4.6 mmol), 5-chloro-2-methoxy-benzoic acid (1.3 g, 6.9 mmol) in PPA (30 mL) was allowed to stir at 200° C. for 5 hours. The mixture was poured to ice and neutralized with KOH. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4. The organic phase was concentrated to provide 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol (300 mg, yield: 27%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.20 (d, J=2.5 Hz, 1H), 7.73˜7.70 (m, 2H), 7.44 (dd, J=8.8, 2.6 Hz, 1H), 7.34˜7.32 (m, 2H), 7.10 (d, J=8.8 Hz, 1H). MS (M+H)+: 245.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic phase was concentrated

出典と根拠

ORDレコード
ord-855e7ec547f94428aa6dd0d58eabbd74
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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