Diethyl Ether → 2-(2-Chlorophenyl)-5-[2-(1-methyl-5-nitroimidazol-2-yl)-vinyl]-1,3,4-thiadiazole

HRID 1856190Notes

Reaction equation

HRID 1856190 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])=[N:5][N:6]=1.[CH3:14][N:15]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=[C:16]1[CH:23]=O.CCOCC>C(O)(=O)C.C(OC(=O)C)(=O)C.[Cl-].[Cl-].[Zn+2]>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[S:3][C:2]([CH:1]=[CH:23][C:16]2[N:15]([CH3:14])[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=2)=[N:6][N:5]=1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 43133201,3,4-Thiadiazole, 2-(2-chlorophenyl)-5-methyl-

Product 1

HCID 705852612-(2-Chlorophenyl)-5-[2-(1-methyl-5-nitroimidazol-2-yl)-vinyl]-1,3,4-thiadiazoleYield 53.4%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

21 g of 2-methyl-5-(2-chlorophenyl)-1,3,4-thiadiazole and 15.5 g of 1-methyl-5-nitroimidazole-2-carboxaldehyde are heated with 0.5 g of ZnCl2 in a mixture of 100 ml of acetic acid and 50 ml of acetic anhydride for 6 hours at reflux temperature. After cooling, ether is added to the reaction mixture, and the precipitated solid is washed with water and recrystallized from dimethylformamide. 18.5 g of product is obtained, corresponding to 53% of the theory. The compound melts at 239° C.

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. washthe precipitated solid is washed with water
  4. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-d65725c68b8143cb8fd95170ce28354e
Source dataset
uspto-grants-1980_08
Patent number
US04218460

Reaction notes

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