Anisole → HCID 19973436, compound

HRID 1757121Notes

Reaction equation

HRID 1757121 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1([C:23]([S:26]CC1C=CC(OC)=CC=1)=[N:24][CH3:25])[N:15]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=[CH:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1([N:15]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=[CH:16]1)[C:23](=[S:26])[NH:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 15290093HCID 15290093, compound

Product 1

HCID 19973436HCID 19973436, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

6.15 g (12.4 mmol) of the 2-benzyloxy-1-((4-methoxybenzylthio)(methylimino)methyl)-1-(4-nitro-imidazol-1-yl)cyclohexane prepared in the Preparative Example 14 was dissolved in 25 ml of trifluoroacetic acid under cooling with ice, followed by the addition of 5 ml of anisole. The obtained mixture was stirred at 0° C. for 10 minutes to give a dark-brown solution, which was pored onto a mixture comprising a saturated aqueous solution of sodium hydrogencarbonate and ice. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous sodium sulfate, and concentrated in a vacuum. The residue (8.02 g) was purified by silica gel column chromatography [solvent: dichloromethane/acetone (40:1)], and recrystallized from dichloromethane/diisopropyl ether to give 3.14 g of the title compound as a colorless crystal (yield: 67%).

Workup

  1. temperatureunder cooling with ice
  2. customto give a dark-brown solution, which
  3. extractionThe obtained mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with a saturated aqueous solution of common salt
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in a vacuum
  7. customThe residue (8.02 g) was purified by silica gel column chromatography [solvent: dichloromethane/acetone (40:1)]
  8. customrecrystallized from dichloromethane/diisopropyl ether

Sources & evidence

ORD record
ord-81f9968b7f554cfba6347320e4d787b1
Source dataset
uspto-grants-1995_08
Patent number
US05444066

Reaction notes

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