Potassium Permanganate → HCID 54564877, compound

HRID 2247906Notes

Reaction equation

HRID 2247906 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH:9]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]=1[NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25].[O-][Mn](=O)(=O)=O.[K+]>[O-2].[Mn+4].[O-2].ClCCl>[CH:2]([C:3]1[CH:8]=[C:7]([CH:9]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][C:4]=1[NH:21][C:22](=[O:26])[O:23][CH2:24][CH3:25])=[O:1]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 54543058HCID 54543058, compound

Product 1

HCID 54564877HCID 54564877, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.9 parts of intermediate 61, namely ethyl [2-(hydroxymethyl)-4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]carbamate, in 798 parts of dichloromethane were added 21.5 parts of manganese(IV)oxide and a catalytic amount of KMnO4. After stirring for 18 hours at room temperature, the reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was co-evaporated with methylbenzene and was further purified by column chromatography (silica gel; CHCl3 /CH3OH 95:5). The eluent of the desired fraction was evaporated and the residue was taken up in ethyl acetate. This solution was concentrated and left to crystallize. The crystallized product was filtered off, stirred in 2,2'-oxybispropane and dried in vacuo, yielding 2.85 parts (48.8%) of ethyl [2-formyl-4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]carbamate; mp. 107.0° C. (interm. 62).

Workup

  1. filtrationthe reaction mixture was filtered over diatomaceous earth
  2. customthe filtrate was evaporated
  3. customwas further purified by column chromatography (silica gel; CHCl3 /CH3OH 95:5)
  4. customThe eluent of the desired fraction was evaporated
  5. concentrationThis solution was concentrated
  6. waitleft
  7. customto crystallize
  8. filtrationThe crystallized product was filtered off
  9. stirringstirred in 2,2'-oxybispropane
  10. customdried in vacuo

Sources & evidence

ORD record
ord-7d4eca1f0a294d8e853f1f84eef1e3c4
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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