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

HRID 350586Notes

Reaction equation

HRID 350586 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

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 ΕC. HCl gas was bubbled through followed by stirring for 24 hours at 50 ΕC. The mixture was stirred for 8 more days at 50 ΕC with addition of HCl-gas every 24 hours, followed by stirring at 50 ΕC for 4 more days. More HCl-gas was added and stirred for 3 more days at 50 ΕC. The solution was cooled to 0 ΕC and filtered. The residue was mixed with ethanol (96%, 200 ml) and the title compound, Compound 6, was isolated by filration. Yield: 23.1 g (62%). NMR confirmed the structure of the title compound.

Workup

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

Sources & evidence

ORD record
ord-d47d920d66a24f8396e43f6990bae139
Source dataset
uspto-grants-2007_02
Patent number
US07182934B2

Reaction notes

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