Benzyl Bromide → HCID 15290093, compound

HRID 1440242Notes

Reaction equation

HRID 1440242 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][S:8][C:9](=[N:25][CH3:26])[C:10]2([N:17]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[N:19]=[CH:18]3)[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[OH:16])=[CH:5][CH:4]=1.[H-].[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1>[CH2:31]([O:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C:10]1([C:9]([S:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=1)=[N:25][CH3:26])[N:17]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[N:19]=[CH:18]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 15290092HCID 15290092, compound

Product 1

HCID 15290093HCID 15290093, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 42.76 g (106 mmol) of the 2-((4-methoxybenzylthio)(methylimino)methyl) -2-(4-nitroimidazol-1-yl)cyclohexanol prepared in the Preparative Example 13 in 300 ml of tetrahydrofuran was dropped into a suspension of 5.13 g (60% dispersion in mineral oil, 128 mmol) of sodium hydride in 60 ml of tetrahydrofuran in a nitrogen atmosphere at room temperature in 20 minutes. The obtained mixture was further stirred at 50° C. for 10 minutes, followed by the addition of 13.2 ml (111 mmol) of benzyl bromide at 50° C. The obtained mixture was stirred at 50° C. for one hour and then under reflux by heating for 20 hours. The obtained brown suspension was cooled by allowing to stand, and poured onto ice-water. The obtained mixture was extracted with ethyl acetate. The obtained organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate, and concentrated in a vacuum. The obtained residue (55.8 g) was purified by silica gel column chromatography [solvent: benzene/acetone (25:1 to 5:1)] to give 6.15 g of the title compound as a brown oil (yield: 12%).

Workup

  1. stirringThe obtained mixture was stirred at 50° C. for one hour
  2. temperatureunder reflux
  3. temperatureby heating for 20 hours
  4. temperatureThe obtained brown suspension was cooled
  5. additionpoured onto ice-water
  6. extractionThe obtained mixture was extracted with ethyl acetate
  7. washThe obtained organic phase was washed with a saturated aqueous solution of common salt
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in a vacuum
  10. customThe obtained residue (55.8 g) was purified by silica gel column chromatography [solvent: benzene/acetone (25:1 to 5:1)]

Sources & evidence

ORD record
ord-6858711a1a45409aa01b79c9a86fcdf5
Source dataset
uspto-grants-1996_03
Patent number
US05498634

Reaction notes

Loading…