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O-Phenylenediamine → 2-[4-[4-(4-Phenyl-1-piperazinyl)-1-butynyl]phenyl]-1H-benzimidazole

HRID 375528
노트
인쇄 미리보기

반응식

HRID 375528 반응식
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[C:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(O)[O-].[Na+].[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH2:37]>CO>[NH3:7].[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[C:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]4[NH:37][C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=5[N:30]=4)=[CH:19][CH:18]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7243O-PhenylenediamineHCID 189930464-[4-(4-Phenylpiperazin-1-yl)but-1-ynyl]benzaldehydeHCID 23665763Sodium Bisulfite

생성물 2

HCID 222AmmoniaHCID 189930372-[4-[4-(4-Phenyl-1-piperazinyl)-1-butynyl]phenyl]-1H-benzimidazole수율 85.7%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

A mixture of 4-[4-(4-phenylpiperazin-1-yl)but-1-ynyl]benzaldehyde (Example B) (1.28 g), sodium bisulfite (0.4 g) and 1,2-diaminobenzene (0.43 g) is stirred in methanol (50 mL) at reflux for 18 hours. The mixture is filtered and the solvent evaporated. The residue is purified by chromatography on silica gel eluting with 200:8:1 dichloromethane:ethanol:0.880 aqueous ammonia to give 0.70 g of the title compound as a tan solid; mp 247°-248° C.

후처리

  1. temperatureat reflux for 18 hours
  2. filtrationThe mixture is filtered
  3. customthe solvent evaporated
  4. customThe residue is purified by chromatography on silica gel eluting with 200:8:1 dichloromethane

출처 및 근거

ORD 기록
ord-0be8c9b0f4e349d4932b1596cfacdb5a
출처 데이터셋
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05486517

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