HCID 69522172, compound → HCID 43299414, compound

HRID 856694Notes

Reaction equation

HRID 856694 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[N:5][N:6]=1>C(O)(=O)C>[CH3:1][C:2]1[O:3][C:4]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[N:5][N:6]=1

Participants

3

Reactant 1

HCID 69522172HCID 69522172, compound

Product 1

HCID 43299414HCID 43299414, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2-methyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,3,4-oxadiazole (3.3 g) was added acetic acid (33 ml), and reduced iron (9.9 g) was added to the mixture, and the mixture was stirred for 240 hours at room temperature. The mixture was filtered with Celite, and the mixture was washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]sulfanyl]aniline (2.2 g).

Workup

  1. additionwas added to the mixture
  2. filtrationThe mixture was filtered with Celite
  3. washthe mixture was washed with ethyl acetate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-10436f91c58a4eb380859f838f56cb22
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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