Hydrochloric Acid → 1-Methyl-5-nitro-2-imidazolecarboxaldehyde-4-methylsemicarbazone

HRID 1730181Notes

Reaction equation

HRID 1730181 reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH:10]=O.[CH3:12][NH:13][C:14](=[O:17])[NH:15][NH2:16].Cl>O.C(O)C>[CH3:12][NH:13][C:14](=[O:17])[NH:15][N:16]=[CH:10][C:3]1[N:2]([CH3:1])[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 256005n-methylhydrazinecarboxamide

Product 1

HCID 539937051-Methyl-5-nitro-2-imidazolecarboxaldehyde-4-methylsemicarbazoneYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 8.5 grams (0.055 mole) of 1-methyl-5-nitro-2-imidazolecarboxaldehyde in 50 ml. of ethanol is added a solution of 5.0 grams (0.056 mole) of 4-methylsemicarbazide in 25 ml. of ethanol and 10 ml. of water containing 2-4 drops of concentrated hydrochloric acid. The resulting solution is heated at 60°-70° C. until a yellow solid starts to separate and then stored at 0° C. for 1 hour; 12.2 grams (98%) of 1-methyl-5-nitro-2-imidazolecarboxaldehyde-4-methylsemicarbazone is obtained melting at 221°-223° C.

Workup

  1. temperatureThe resulting solution is heated at 60°-70° C. until a yellow solid starts
  2. customto separate

Sources & evidence

ORD record
ord-776596e9e1b64cf19b2494a684e86da2
Source dataset
uspto-grants-1976_11
Patent number
US03991200

Reaction notes

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