1-Methyl-5-nitro-1H-imidazole-2-carbaldehyde → HCID 54453104, compound

HRID 1856194Notes

Reaction equation

HRID 1856194 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:18][C:17]([CH3:19])=[N:16][N:15]=1)[CH3:13]>C(O)(=O)C.C(OC(=O)C)(=O)C.[Cl-].[Cl-].[Zn+2]>[CH2:12]([C:14]1[S:18][C:17]([CH:19]=[CH:10][C:3]2[N:2]([CH3:1])[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=2)=[N:16][N:15]=1)[CH3:13]

Participants

6

Reactant 2

HCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 10964522HCID 10964522, compound

Product 1

HCID 54453104HCID 54453104, compound

Reagents, catalysts & solvents 3

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

Procedure

A solution of 15.5 g of 1-methyl-5-nitroimidazole-2carboxaldehyde in 50 ml of acetic acid and 25 ml of acetic anhydride is added at reflux temperature over a period of 10 hours to 12.8 g of 5-ethyl-2-methyl-1,3,4-thiadiazole and 0.5 g of ZnCl2 which have been dissolved in 100 ml of acetic acid and 50 ml of acetic anhydride. The mixture is kept at reflux temperature for a further 20 hours and the solvent is then evaporated. The residue is washed with acetone and passed through a ready-to-use silica gel column (Type A of Messrs. Merck) and eluted with CHCl3 /CH3OH=98 : 2. 5.6 g of the abovementioned reaction product with a melting point of 165° C. is obtained; this corresponds to 21% of the theory.

Workup

  1. temperatureat reflux temperature for a further 20 hours
  2. customthe solvent is then evaporated
  3. washThe residue is washed with acetone
  4. washMerck) and eluted with CHCl3 /CH3OH=98 : 2

Sources & evidence

ORD record
ord-f0308d305a6842c29200ab941fb76325
Source dataset
uspto-grants-1980_08
Patent number
US04218460

Reaction notes

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