Stannous chloride dihydrate → HCID 57465381, compound

HRID 1951595Notes

Reaction equation

HRID 1951595 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.O.O.[Sn](Cl)Cl>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 57465380HCID 57465380, compound

Product 1

HCID 57465381HCID 57465381, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

under an N2 atmosphere, was 4-(3-chlorophenyl)-2-(4-nitrophenyl)oxazole (2.65 g, 8.81 mmol) suspended in methanol (20.0 mL) and tin(II) chloride dihydrate (7.95 g, 35.3 mmol) was added. The reaction was stirred at room temperature for ca. 72 h. LC-MS showed the reaction was not complete. The reaction was heated to 60° C. for 5 hours. The reaction was then diluted with ethyl acetate and washed with 0.1N HCl, followed by 5% NaHCO3 and brine. The organic layer was then dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by chromatography on silica gel, eluting with 20% to 40% ethyl acetate in hexanes. The resulting solid was triturated with ethyl acetate/hexanes and the resulting solid was collected by filtration to afford 4-(4-(3-chlorophenyl)oxazol-2-yl)benzenamine (0.898 g, 37.6% yield). ESI m/z=271.0 (M+H+).

Workup

  1. temperatureThe reaction was heated to 60° C. for 5 hours
  2. washwashed with 0.1N HCl
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by chromatography on silica gel
  7. washeluting with 20% to 40% ethyl acetate in hexanes
  8. customThe resulting solid was triturated with ethyl acetate/hexanes
  9. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-bc9ab9b303c7466ab13ccd85e44e418c
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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