Stannous chloride dihydrate → HCID 18950796, compound

HRID 1492450Notes

Reaction equation

HRID 1492450 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][O:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[N:12][O:13][CH:14]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 18950797HCID 18950797, compound

Product 1

HCID 18950796HCID 18950796, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-nitrophenyloxadiazole (2.87 g, 0.015 mol, prepared according to Lin et al., J. Org. Chem., 1979, 44, 4160) and SnCl2.2H2O (16.92 g, 0.075 mol) in 75 mL of ethyl acetate was heated at 75° C. for 30 minutes. The yellow reaction mixture was cooled to room temperature, poured into ice-water and the pH was made slightly basic (pH 7-8) by the addition of 5% NaHCO3. The reaction mixture was then extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo. The remaining yellow solid was triturated with hexane, collected and dried to yield 2.07 g of the title A compound, m.p. 97°-99° C. TLC, silica gel, EtOAc/hexanes (2:1), Rf =0.55; M.S. (M+H)+ at 162, M.W. 161. This compound was used without further purification.

Workup

  1. temperatureThe yellow reaction mixture was cooled to room temperature
  2. extractionThe reaction mixture was then extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe remaining yellow solid was triturated with hexane
  6. customcollected
  7. customdried
  8. customto yield 2.07 g of the title A compound, m.p. 97°-99° C
  9. customThis compound was used without further purification

Sources & evidence

ORD record
ord-ec8a9e0a40584238a6df9f51b040b6d4
Source dataset
uspto-grants-1994_12
Patent number
US05374643

Reaction notes

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