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Benzylamine → 5-Amino-1-benzyl-1H-imidazole-4-carbonitrile

HRID 1989805
Notes
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Reaction equation

HRID 1989805 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N/C(/C#N)=[C:11](\[C:14](=[NH:18])OCC)/[C:12]#[N:13].Cl.[NH2:22][C:23]1C=CC=CC=1.[OH-].[Na+]>C(O)C>[NH2:18][C:14]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:23]=[N:22][C:11]=1[C:12]#[N:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8870Benzenamine hydrochloride (1:1)HCID 14798Sodium HydroxideHCID 86609248HCID 86609248, compound

Product 1

HCID 3432245-Amino-1-benzyl-1H-imidazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Conditions

Temperature
10 °C

Procedure

Benzylamine (2.86 ml, 26.3 mmol) was added dropwise to a solution of ethyl [(Z)-2-amino-1,2-dicyanovinyl]imidoformate (4.1 g, 25.0 mmol) and aniline hydrochloride (50 mg) in ethanol (80 ml), stirring at 10° C. and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was added dropwise to 1M sodium hydroxide (50 ml), stirring at 10° C. and the resultant suspension stirred at room temperature for 18 hours. The solid was collected by filtration, washed with water and dried in vacuo. The title compound was obtained as an off white solid (3.6 g, 18.2 mmol, 73%).

Workup

  1. stirringthe reaction mixture stirred at room temperature for 18 hours
  2. stirringstirring at 10° C.
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-edc45f5d6c3b40db9e696a650759e1f1
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07642350B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes