NSC315854 → HCID 12433847, compound

HRID 261954Notes

Reaction equation

HRID 261954 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:13]2[N:14](C=C)[CH:15]=[CH:16][N:17]=2)[OH:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=O.[K+]>C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)[OH:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 330102NSC315854HCID 516875Potassium Permanganate2×

Product 1

HCID 12433847HCID 12433847, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

This compound was prepared by the procedure described in Example XXI B using 22.6 g. (0.068 mol) of α-(p-tert.-butylphenyl)-α-phenyl-1-vinylimidazole-2-methanol, 820 ml. of 4% aqueous potassium permanganate and 11 g. of solid potassium permanganate (total permanganate 0.214 mol). After the manganese dioxide had been filtered off, the excess of potassium permanganate in the filtrate was reduced to manganese dioxide by addition of sodium bisulphite. The precipitate was filtered off and the organic solvents were distilled off. The remainder of the filtrate was poured into water and the oil thus obtained was dissolved in diethyl ether. The solution was washed four times with water and dried over sodium sulphate and the solvent was distilled off. The resulting oil was taken up in as little acetone as possible and brought to crystallisation by adding petroleum ether (boiling range 28°-40° C.). Melting point 166°-166° C.

Workup

  1. customThis compound was prepared by the procedure
  2. filtrationAfter the manganese dioxide had been filtered off
  3. additionthe excess of potassium permanganate in the filtrate was reduced to manganese dioxide by addition of sodium bisulphite
  4. filtrationThe precipitate was filtered off
  5. distillationthe organic solvents were distilled off
  6. additionThe remainder of the filtrate was poured into water
  7. customthe oil thus obtained
  8. washThe solution was washed four times with water
  9. dry with materialdried over sodium sulphate
  10. distillationthe solvent was distilled off
  11. custombrought to crystallisation
  12. additionby adding petroleum ether (boiling range 28°-40° C.)

Sources & evidence

ORD record
ord-13fd7df00a43415eabb00a5c345976c8
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

Loading…