Water → HCID 54455049, compound

HRID 1856189Notes

Reaction equation

HRID 1856189 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:6]=1.[CH3:13][N:14]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=[C:15]1[CH:22]=O.C(OC(=O)C)(=O)C.O>C(O)(=O)C.[Cl-].[Cl-].[Zn+2]>[C:7]1([C:4]2[S:3][C:2]([CH:1]=[CH:22][C:15]3[N:14]([CH3:13])[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=3)=[N:6][N:5]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 974251,3,4-Thiadiazole, 2-methyl-5-phenyl-

Product 1

HCID 54455049HCID 54455049, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

17.6 g of 2-methyl-5-phenyl-1,3,4-thiadiazole, 15.5 g of 1-methyl-5-nitroimidazole-2-carboxaldehyde and 0.5 g of ZnCl2 are heated in 100 ml of acetic acid and 50 ml of acetic anhydride for 7 hours at reflux temperature. After water has been added to the reaction mixture, the precipitated solid is recrystallized from glacial acetic acid. 17.5 g of a product melting at 257° C. is obtained, corresponding to 56% of the theory.

Workup

  1. customthe precipitated solid is recrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-4b151c84c3864758af5e4ae1bc42281a
Source dataset
uspto-grants-1980_08
Patent number
US04218460

Reaction notes

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