Water → HCID 59799786, compound

HRID 1912015Notes

Reaction equation

HRID 1912015 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-bf03a76f698a4c5aa1b236c479fd44a7
Source dataset
uspto-grants-2013_12
Patent number
US08604218B2

Reaction notes

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