Acetic Anhydride → HCID 53739186, compound

HRID 1856195Notes

Reaction equation

HRID 1856195 reaction equation
[CH2:1]([C:14]1[S:15][C:16]([CH3:19])=[N:17][N:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:20][N:21]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]1[CH:29]=O.C(OC(=O)C)(=O)C>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH2:1]([C:14]1[S:15][C:16]([CH:19]=[CH:29][C:22]2[N:21]([CH3:20])[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=2)=[N:17][N:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 784871-Methyl-5-nitro-1H-imidazole-2-carbaldehydeHCID 233463742-Methyl-5-tridecyl-1,3,4-thiadiazole

Product 1

HCID 53739186HCID 53739186, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

8.45 g of 2-tridecyl-5-methyl-1,3,4-thiadiazole, 4.65 g of 1-methyl-5-nitroimidazole-2-carboxaldehyde and 0.5 g of zinc chloride are heated in 40 ml of acetic acid and 15 ml of acetic anhydride for 24 hours at reflux temperature. After the solvent has been removed, the residue is recrystallized from alcohol. 7.1 g of product is obtained, corresponding to 61% of the theory. The melting point is 91° C.

Workup

  1. customAfter the solvent has been removed
  2. customthe residue is recrystallized from alcohol

Sources & evidence

ORD record
ord-0fb3f5fddbad49e8bda16a28667d452a
Source dataset
uspto-grants-1980_08
Patent number
US04218460

Reaction notes

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