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

HRID 1776876노트

반응식

HRID 1776876 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

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온도
200 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-855e7ec547f94428aa6dd0d58eabbd74
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265773B2

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