Methane → 5-Methyl-2-(4-(4-methylphenyl)-3-thienyl)-[1,3,4]oxadiazole

HRID 398792Notes

Reaction equation

HRID 398792 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]3[NH:17][N:16]=NN=3)=[CH:10][S:11][CH:12]=2)=[CH:4][CH:3]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19].C(=O)(O)[O-].[Na+].C>C(OCC)(=O)C>[CH3:19][C:18]1[O:20][C:13]([C:9]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[CH:12][S:11][CH:10]=2)=[N:17][N:16]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178423922HCID 178423922, compound

Product 1

HCID 189689025-Methyl-2-(4-(4-methylphenyl)-3-thienyl)-[1,3,4]oxadiazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(4-(4-methylphenyl)-3-thienyl)-tetrazole (3.3 g, 13.2 mmol) and acetic anhydride (50 ml) was heated at reflux temperature for 1 h. The resulting solution was evaporated in vacuo to give an oily residue which was dissolved into ethyl acetate (100 ml). The organic solution was vashed with a sodium bicarbonate solution (100 ml), treated with activated charcoal and dried (MgSO4). Filtration and evaporation in vacuo afforded 3.4 g of 5-methyl-2-(4-(4-methylphenyl)-3-thienyl)-[1,3,4]- oxadiazole as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. customThe resulting solution was evaporated in vacuo
  4. customto give an oily residue which
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and evaporation in vacuo

Sources & evidence

ORD record
ord-81765c7f64d4451c9f42fbbca691c5ab
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

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