Methanol → HCID 22414887, compound

HRID 1721436Notes

Reaction equation

HRID 1721436 reaction equation
[NH2-].[Na+].[CH2:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=1Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>O1CCCC1>[CH2:3]([NH:10][C:23]1[CH:24]=[C:19]([O:18][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:20]=[CH:21][C:22]=1[CH3:25])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7504BenzylamineHCID 24533Sodium amideHCID 107312131-(benzyloxy)-2-bromo-4-methylbenzene

Product 1

HCID 22414887HCID 22414887, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

100.0 g (2.56 mol) of sodium amide was added to 700 g (6.53 mol) of benzylamine under an argon atmosphere, and the mixture was stirred for 10 minutes at 60° C. A solution of 222.20 g (0.801 mol) of 1-benzyloxy-2-bromo-4-methylbenzene was dissolved in 400 ml of tetrahydrofuran was added dropwise to the above mixture over 50 minutes. The mixture was stirred for 50 minutes while maintaining the temperature at 60° C. Methanol was added under cooling with ice, and the mixture was poured into ice water. The reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporating the solvent was purified by column chromatography (silica gel, 10:1 mixture of n-hexane and ethyl acetate). The crude product thus obtained was recrystallized from n-hexane to obtain 175.80 g (yield: 72.3%) of the title compound as colorless needles.

Workup

  1. additionwas added dropwise to the above mixture over 50 minutes
  2. stirringThe mixture was stirred for 50 minutes
  3. temperaturewhile maintaining the temperature at 60° C
  4. temperatureunder cooling with ice
  5. extractionThe reaction mixture was extracted with ethyl acetate-water
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe residue obtained
  9. customby evaporating the solvent
  10. customwas purified by column chromatography (silica gel, 10:1 mixture of n-hexane and ethyl acetate)
  11. customThe crude product thus obtained
  12. customwas recrystallized from n-hexane

Sources & evidence

ORD record
ord-314e7fcbd1fb4391a79eae0406d46bbf
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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