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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
Notes
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Reaction equation

HRID 452150 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

[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%).

Workup

  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

Sources & evidence

ORD record
ord-97b6ec24bd07486795ab89488ac58b77
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486980B2

Reaction notes

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