2-(Ethoxymethylene)propanedinitrile → 1H-Benzimidazole-6-carbonitrile

HRID 1363124Notes

Reaction equation

HRID 1363124 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[CH2:11](OC=C(C#N)C#N)C>C(O)(C)C>[N:10]1[C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[NH:1][CH:11]=1

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 2239061H-Benzimidazole-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 3,4-diaminobenzonitrile (2) (1.0 g) and (ethoxymethylene)malononitrile (1.4 g) was refluxed in 50 mL of isopropyl alcohol for 16 h. The mixture was concentrated in vacuo to provide the title compound, 3H-benzo[d]imidazole-5-carbonitrile (3).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d9aadab0f5414477931c8f7a1a189282
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

Loading…