Hydrogen Peroxide → Ammonia

HRID 2118058Notes

Reaction equation

HRID 2118058 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][S:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1.[OH:28]O>FC(F)(F)C(O)C(F)(F)F>[NH3:6].[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]3[C:10]([CH2:11][S:12](=[O:28])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[CH:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 21925607HCID 21925607, compound

Product 2

HCID 222AmmoniaHCID 21925554HCID 21925554, compound

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

To a solution of the sulphide of example 107 (150 mg, 0.38 mmol) in 1,1,1,3,3,3-Hexafluoro-propan-2-ol (5 ml) was added a 30% aqueous solution of hydrogen peroxide (0.09 ml). The resulting reaction mixture was stirred at room temperature for 1 hour before partitioning with aqueous sodium sulfite. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated. The resulting residue was purified by column chromatography on silica gel using dichloromethane:Methanol:0.880 ammonia (95:5:0.5) as eluant, to afford the title compound as an off-white foam (64 mg)

Workup

  1. customThe resulting reaction mixture
  2. custombefore partitioning with aqueous sodium sulfite
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3803acc963b44b64a32d92a247e2d048
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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