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

HRID 1989805Notes

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]

Participants

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

stirringthe reaction mixture stirred at room temperature for 18 hours
stirringstirring at 10° C.
filtrationThe solid was collected by filtration
washwashed with water
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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