1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde → HCID 54243556, compound

HRID 1856192Notes

Reaction equation

HRID 1856192 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:5][N:6]=1.[CH3:13][N:14]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=[C:15]1[CH:22]=O>C(O)(=O)C.C(OC(=O)C)(=O)C.[Cl-].[Cl-].[Zn+2]>[N:10]1[CH:11]=[CH:12][C:7]([C:4]2[S:3][C:2]([CH:1]=[CH:22][C:15]3[N:14]([CH3:13])[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=3)=[N:6][N:5]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 23346364HCID 23346364, compound

Product 1

HCID 54243556HCID 54243556, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

8.8 g of 2-methyl-5-(4-pyridyl)-1,3,4-thiadiazole and 7.7 g of 1-methyl-5-nitroimidazole-2-carboxaldehyde are heated with 0.2 g of ZnCl2 in a mixture of 50 ml of glacial acetic acid and 25 ml of acetic anhydride for 6 hours at reflux temperature. After cooling, the precipitated solid is suction filtered, washed with concentrated ammonia and recrystallized from dimethylformamide. The melting point of the product obtained is 240°-241° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. washwashed with concentrated ammonia
  5. customrecrystallized from dimethylformamide
  6. customThe melting point of the product obtained
  7. customis 240°-241° C.

Sources & evidence

ORD record
ord-2905a901746b42e0821b1f3b959c39e7
Source dataset
uspto-grants-1980_08
Patent number
US04218460

Reaction notes

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