4-Azidomethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole → C-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-methylamine

HRID 490750Notes

Reaction equation

HRID 490750 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10])=[N+]=[N-].[H][H]>C(OCC)(=O)C.O=[Pt]=O>[CH3:10][C:9]1[O:8][C:7]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)=[N:6][C:5]=1[CH2:4][NH2:1]

Participants

5

Reactant 2

HCID 587657284-Azidomethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 58765787C-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-methylamineYield 84.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-azidomethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole (1.70 g) and PtO2 (0.106 g) in ethyl acetate (50 mL) at room temperature under 60 psi of hydrogen for 5 hrs, the reaction mixture is filtered through celite and filtrate is concentrated giving the title compound (1.3 g, 84.2% yield).

Workup

  1. filtrationthe reaction mixture is filtered through celite and filtrate
  2. concentrationis concentrated

Sources & evidence

ORD record
ord-47e393fd217a44e9a6c6d06458a848f4
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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