HCID 23725533, compound → HCID 23725535, compound

HRID 2219424Notes

Reaction equation

HRID 2219424 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[C:15]([CH2:27][OH:28])[N:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH:17]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]1[N:14]=[C:15]([CH:27]=[O:28])[N:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH:17]=1

Participants

4

Reactant 1

HCID 23725533HCID 23725533, compound

Product 1

HCID 23725535HCID 23725535, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(5-methyl-3-phenyl-isoxazol-4-yl)-1-(4-nitro-phenyl)-1H-imidazol-2-yl]-methanol (50 mg, 0.13 mmol) in DCM (3 mL) was added manganese(IV) oxide (46 mg, 0.5 mmol) and the resulting mixture stirred at room temperature for 5 h. The mixture was then filtered over dicalite and washed with DCM. Then another aliquot of manganese(IV) oxide (46 mg, 0.5 mmol) was added and the mixture stirred overnight and then another aliquot of manganese(IV) oxide (120 mg, 1.3 mmol) was added and the mixture stirred for 5 h. The mixture was then filtered over dicalite and washed with DCM and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (16.4 mg, 33%) which was obtained as a yellow gum. MS: m/e=375.3 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered over dicalite
  2. washwashed with DCM
  3. stirringthe mixture stirred overnight
  4. stirringthe mixture stirred for 5 h
  5. filtrationThe mixture was then filtered over dicalite
  6. washwashed with DCM
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20)

Sources & evidence

ORD record
ord-d8bdba015b824b129408829a487cfdbf
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

Loading…