Hydrochloric Acid → 5-chloro-2-(4-nitrophenyl)-1H-Imidazole-4-carboxaldehyde

HRID 1385809Notes

Reaction equation

HRID 1385809 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:18]=[CH:17][C:8]([CH:9]=[N:10][C:11](=[C:14](Cl)Cl)[C:12]#[N:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[O:19]1CCOCC1>>[Cl:1][C:12]1[N:13]=[C:9]([C:8]2[CH:17]=[CH:18][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[NH:10][C:11]=1[CH:14]=[O:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 122907202-(4-Nitrobenzylidene)amino-3,3-dichloropropenonitrile

Product 1

HCID 1785200115-chloro-2-(4-nitrophenyl)-1H-Imidazole-4-carboxaldehyde

Conditions

Temperature
50 °C

Procedure

HCl gas was bubbled through a solution of 2-(4-nitrobenzylidene)amino-3,3-dichloro-propenonitrile (40.0 g, 0.148 mole) in dioxane (500 ml) at room temperature. The mixture was stirred for 23 hours at 50° C. HCl gas was bubbled through followed by stirring for 24 hours at 50° C. The mixture was stirred for 8 more days at 50° C. with addition of HCl-gas every 24 hours, followed by stirring at 50° C. for 4 more days. More HCl-gas was added and stirred for 3 more days at 50° C. The solution was cooled to 0° C. and filtered. The residue was mixed with ethanol (96%, 200 ml) and the title compound, Compound 6, was isolated by filration.

Workup

  1. customHCl gas was bubbled
  2. stirringby stirring for 24 hours at 50° C
  3. stirringThe mixture was stirred for 8 more days at 50° C. with addition of HCl-gas every 24 hours
  4. stirringby stirring at 50° C. for 4 more days
  5. additionMore HCl-gas was added
  6. stirringstirred for 3 more days at 50° C
  7. temperatureThe solution was cooled to 0° C.
  8. filtrationfiltered
  9. additionThe residue was mixed with ethanol (96%, 200 ml)

Sources & evidence

ORD record
ord-93b869619e314ae9ba73a42c1771a3c8
Source dataset
uspto-grants-2001_07
Patent number
US06264914B1

Reaction notes

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