1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde → 2-Ethyl-5-[1-methyl-2-(1-methyl-5-nitroimidazol-2-yl)-vinyl]-1,3,4-thiadiazole

HRID 1856196Notes

Reaction equation

HRID 1856196 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.[CH2:12]([C:14]1[S:15][C:16]([CH2:19][CH3:20])=[N:17][N:18]=1)[CH3:13]>C(O)(=O)C.C(OC(=O)C)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH2:12]([C:14]1[S:15][C:16]([C:19]([CH3:20])=[CH:10][C:3]2[N:2]([CH3:1])[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=2)=[N:17][N:18]=1)[CH3:13]

Participants

6

Reactant 2

HCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 64516672,5-Diethyl-1,3,4-thiadiazole

Product 1

HCID 30861172-Ethyl-5-[1-methyl-2-(1-methyl-5-nitroimidazol-2-yl)-vinyl]-1,3,4-thiadiazoleYield 34.6%

Reagents, catalysts & solvents 3

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

Procedure

4.65 g of 1-methyl-5-nitroimidazole-2-carboxaldehyde, which has been dissolved in 80 ml of acetic acid and 35 ml of acetic anhydride, is dripped into 17.1 g of 2,5-diethyl-1,3,4thiadiazole, which has been dissolved in a mixture of 60 ml of acetic acid, 25 ml of acetic anhydride and 0.5 g of zinc chloride, over a period of 5 hours at reflux temperature. After being heated for a further 24 hours at reflux temperature the reaction mixture is concentrated by removing the solvent and water is added. The precipitated reaction product is then subjected to sublimation and recrystallized from propanol. 2.9 g of product, corresponding to 35% of the theory, is obtained. The compound melts at 125° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter being heated for a further 24 hours
  3. temperatureat reflux temperature the reaction mixture
  4. concentrationis concentrated
  5. customby removing the solvent and water
  6. additionis added
  7. customThe precipitated reaction product
  8. customrecrystallized from propanol

Sources & evidence

ORD record
ord-e244fbacfed84fe0a5bfa818de89b7a3
Source dataset
uspto-grants-1980_08
Patent number
US04218460

Reaction notes

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