Acetic Acid → HCID 69522172, compound

HRID 856693Notes

Reaction equation

HRID 856693 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]2[NH:16][N:15]=NN=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:17](O)(=[O:19])[CH3:18]>>[CH3:18][C:17]1[O:19][C:12]([CH2:11][S:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[N:16][N:15]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 178526720HCID 178526720, compound

Product 1

HCID 69522172HCID 69522172, compound

Procedure

To 5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole (4.0 g) was added anhydrous acetic acid, and the mixture was heated to reflux for 1 hour. After allowing the mixture to be cooled to room temperature, the solvent was removed under reduced pressure. The obtained residue was dissolved in ethyl acetate/THF, washed with an aqueous solution of saturated sodium bicarbonate and saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was washed with hexane/ethyl acetate, to give 2-methyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,3,4-oxadiazole (3.3 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe obtained residue was dissolved in ethyl acetate/THF
  5. washwashed with an aqueous solution of saturated sodium bicarbonate and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-b65dace4438b4c9fb3d510759dc34c02
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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