1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde → HCID 54069604, compound

HRID 1856193Notes

Reaction equation

HRID 1856193 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][C:13]1[S:14][CH:15]=[N:16][N:17]=1>C(O)(=O)C.C(OC(=O)C)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH:10]=[CH:12][C:13]1[S:14][CH:15]=[N:16][N:17]=1

Participants

6

Reactant 2

HCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 142788092-Methyl-1,3,4-thiadiazole

Product 1

HCID 54069604HCID 54069604, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent2×HCID 7918Acetic AnhydrideSolvent2×

Procedure

0.3 g of zinc chloride is added to 15.5 g of 1-methyl-5nitroimidazol-2-carboxaldehyde which has been dissolved in 100 ml of acetic acid and 50 ml of acetic anhydride and the whole is dripped into 10 g of 2-methyl-1,3,4-thiadiazole, which has been dissolved in a mixture of 100 ml of acetic acid and 50 ml of acetic anhydride, over a period of 5 hours at reflux temperature. After 24 hours the reaction mixture is freed of the solvent by evaporation and ether is added. After the reaction product has been washed with water it is recrystallized from xylene. 9.3 of product, corresponding to 39% of the theory, is obtained. The compound melts at 214° C.

Workup

  1. temperatureat reflux temperature
  2. customAfter 24 hours the reaction mixture is freed of the solvent by evaporation and ether
  3. additionis added
  4. washAfter the reaction product has been washed with water it
  5. customis recrystallized from xylene
  6. custom9.3 of product, corresponding to 39% of the theory, is obtained

Sources & evidence

ORD record
ord-1333992633924f4fbb7846ada9aa6f90
Source dataset
uspto-grants-1980_08
Patent number
US04218460

Reaction notes

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