Sodium Methoxide → HCID 18407193, compound

HRID 2271200Notes

Reaction equation

HRID 2271200 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]([N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6]>O1CCCC1>[CH3:29][O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][N:7]([C:5]([O:2][CH3:1])=[O:6])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18407209HCID 18407209, compound

Product 1

HCID 18407193HCID 18407193, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 226 mg of sodium methoxide in 5 ml of tetrahydrofuran was added dropwise a solution of 1.22 g of N-chlorocarbonyl-N-(2-methoxybenzyl)-2-phenoxyaniline in 5 ml of tetrahydrofuran under ice-cooling with stirring, followed by stirring at room temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure, poured into water and extracted with ethyl acetate, and the extract was washed with 5% hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:6) and recrystallized from ethyl acetate to give 1.18 g of N-(2-methoxybenzyl)-N-methoxycarbonyl-2-phenoxyaniline.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 20 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. washthe extract was washed with 5% hydrochloric acid
  7. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  8. customAfter removal of the drying agent
  9. filtrationby filtration
  10. concentrationthe solvent was concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:6)
  12. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d7f32ec008824262a7ea8d0ae26b0ecb
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

Loading…