Water → HCID 59799786, compound

HRID 656550Notes

Reaction equation

HRID 656550 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([NH2:15])=[N:12][O:13][N:14]=2)=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)Cl.O>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([NH2:15])=[N:12][O:13][N:14]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 14021895HCID 14021895, compound

Product 1

HCID 59799786HCID 59799786, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Nitrophenyl)-1,2,5-oxadiazol-3-amine (0.500 g, 2.42 mmol), tin dichloride (1.61 g, 8.49 mmol), and water (0.306 mL, 17.0 mmol) were combined in ethyl acetate (20 mL) in a round bottom flask, and the mixture was stirred at room temperature overnight. The solvent was removed and methylene chloride was added, and the mixture was washed three times with aqueous NaOH. The organic phase was dried over MgSO4, filtered, and concentrated to afford the title compound as a yellow solid (400 mg, 94%).

Workup

  1. customThe solvent was removed
  2. additionmethylene chloride was added
  3. washthe mixture was washed three times with aqueous NaOH
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25e32bbf1015429db1e12b1036b00feb
Source dataset
uspto-grants-2011_12
Patent number
US08071779B2

Reaction notes

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