Diethyl Ether → HCID 70582728, compound

HRID 1856191Notes

Reaction equation

HRID 1856191 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[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:10]1[CH:11]=[CH:12][C:7]([C:4]2[S:3][C:2]([CH:1]=[CH:23][C:16]3[N:15]([CH3:14])[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=3)=[N:6][N:5]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 122781521,3,4-Thiadiazole, 2-(4-chlorophenyl)-5-methyl-

Product 1

HCID 70582728HCID 70582728, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

21 g of 2-methyl-5-(4-chlorophenyl)-1,3,4-thiadiazole and 22.8 g of 1-methyl-5-nitroimidazol-2-carboxaldehyde are heated with 0.5 g of ZnCl2 in a mixture of 100 ml of acetic acid and 50 ml acetic anhydride for 5 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. 27.5 g of product of obtained, corresponding to 77% of the theory. The compound melts at 268° 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-47c3366e5c124ab9ab31385e22319832
Source dataset
uspto-grants-1980_08
Patent number
US04218460

Reaction notes

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