Benzaldehyde → HCID 178510596, compound

HRID 1285225Notes

Reaction equation

HRID 1285225 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]#[N:8].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)C>CO>[C:7]([CH:6]1[NH:5][CH:4]=[N:3][C:2]1=[N:1][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:8]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 787775-amino-1H-imidazole-4-carbonitrile

Product 1

HCID 178510596HCID 178510596, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-amino-1H-imidazol-5-carbonitrile (1.1 g, 0.01 mole) in 25 ml of methanol was added 1.1 grams of benzaldehyde. The reaction mixture was then stirred at ambient temperature for 16 hours, heated on a steam bath for 20 minutes, cooled to ambient temperature, then stirred with 25 ml of diethyl ether. The mixture was filtered and the filtrate concentrated under reduced pressure to a residual solid. The solid was recrystallized from toluene-butanol to give 5-cyano-4-phenylmethylimino-1H-imidazole (0.92 g; mp, 200°-202°).

Workup

  1. temperatureheated on a steam bath for 20 minutes
  2. temperaturecooled to ambient temperature
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure to a residual solid
  5. customThe solid was recrystallized from toluene-butanol

Sources & evidence

ORD record
ord-68b034b1638e47409f472ba33bedbeeb
Source dataset
uspto-grants-1986_01
Patent number
US04565875

Reaction notes

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