Methanol → HCID 13706970, compound

HRID 1721425Notes

Reaction equation

HRID 1721425 reaction equation
[NH2-].[Na+].[CH2:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[C:12]1[CH:13]=[C:14]([CH3:20])[CH:15]=[CH:16][C:17]=1[O:18][CH3:19].CO>O1CCCC1>[CH2:3]([NH:10][C:15]1[CH:16]=[C:17]([O:18][CH3:19])[CH:12]=[CH:13][C:14]=1[CH3:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7504BenzylamineHCID 24533Sodium amideHCID 891432-Bromo-4-methylanisole

Product 1

HCID 13706970HCID 13706970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

20.3 g (0.520 mol) of sodium amide was added to 140 g (1.31 mol) of benzylamine under an argon atmosphere. After stirring under cooling with ice for 20 minutes, a solution of 34.84 g (0.129 mol) of 3-bromo-4-methoxytoluene dissolved in 220 ml of tetrahydrofuran was added dropwise over 90 minutes. The reaction mixture was heated to 60° C. and stirred for 60 minutes. Methanol was added under cooling with ice, followed by further addition of ice water. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized (chloroform-n-hexane) to obtain 26.96 g (yield, 68.4%) of colorless needles of the title compound.

Workup

  1. temperatureunder cooling with ice for 20 minutes
  2. additionwas added dropwise over 90 minutes
  3. stirringstirred for 60 minutes
  4. temperatureunder cooling with ice
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized (chloroform-n-hexane)
  10. customto obtain

Sources & evidence

ORD record
ord-4067dc5978e44d98a95007bd18489a49
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

Loading…