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Hydrazine hydrate (1:1) → (E)-{2-[4-methyl-6-(hydrazinocarbonyl)-2-propylbenzimidazol-1-yl]methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene}acetonitrile

HRID 452150
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HRID 452150 반응식
[C:1]([C:4]1[CH:5]=[C:6]([CH3:35])[C:7]2[N:11]=[C:10]([CH2:12][CH2:13][CH3:14])[N:9]([CH2:15][C:16]3[CH:33]=[CH:32][C:19]4/[C:20](=[CH:29]/[C:30]#[N:31])/[C:21]5[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=5[CH2:23][CH2:24][C:18]=4[CH:17]=3)[C:8]=2[CH:34]=1)(O)=O.[OH2:36].[NH2:37][NH2:38]>ClCCl>[CH3:35][C:6]1[C:7]2[N:11]=[C:10]([CH2:12][CH2:13][CH3:14])[N:9]([CH2:15][C:16]3[CH:33]=[CH:32][C:19]4/[C:20](=[CH:29]/[C:30]#[N:31])/[C:21]5[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=5[CH2:23][CH2:24][C:18]=4[CH:17]=3)[C:8]=2[CH:34]=[C:4]([C:1]([NH:37][NH2:38])=[O:36])[CH:5]=1
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참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 67211448(E)-[2-(6-Carboxy-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

생성물 1

HCID 67210803(E)-{2-[4-methyl-6-(hydrazinocarbonyl)-2-propylbenzimidazol-1-yl]methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene}acetonitrile수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

[step 1] (E)-[2-(6-Carboxy-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (274 mg, 0.59 mmol) obtained in Reference Example B8 was dissolved in dichloromethane (1 mL), N,N′-carbonyldiimidazole (CDI) (107 mg, 0.66 mmol) was added, and the mixture was stirred at room temperature for 20 min. To this mixture was added hydrazine monohydrate (89 mg, 1.77 mmol), and the mixture was stirred at room temperature for 3 hr. The mixture was concentrated under reduced pressure, water (20 mL) was added, and the precipitate was collected by filtration to give (E)-{2-[4-methyl-6-(hydrazinocarbonyl)-2-propylbenzimidazol-1-yl]methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene}acetonitrile (246 mg, 88%).

후처리

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. concentrationThe mixture was concentrated under reduced pressure, water (20 mL)
  3. additionwas added
  4. filtrationthe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-97b6ec24bd07486795ab89488ac58b77
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486980B2

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