Ammonium Chloride → HCID 18407218, compound

HRID 1016585Notes

Reaction equation

HRID 1016585 reaction equation
C[Mg]Cl.O1CCC[CH2:5]1.[C:9]([N:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]=[O:34])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:11])[CH3:10].[Cl-].[NH4+]>O1CCCC1>[C:9]([N:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]([OH:34])[CH3:5])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18407199HCID 18407199, compoundHCID 178420676HCID 178420676, compound

Product 1

HCID 18407218HCID 18407218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of 5.25 ml of 1M methylmagnesium chloride/tetrahydrofuran diluted with 15 ml of tetrahydrofuran was added dropwise a solution of 1.20 g of N-acetyl-N-(2-formylbenzyl)-2-phenoxyaniline in 7 ml of tetrahydrofuran, followed by stirring at room temperature for an hour. The reaction solution was again cooled on ice, and after addition of a saturated aqueous ammonium chloride solution, extracted with ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride solution 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=1:1) to give 1.19 g of N-acetyl-N-[2-(1-hydroxyethyl)benzyl]-2-phenoxyaniline as an oil.

Workup

  1. temperatureThe reaction solution was again cooled on ice
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the drying agent
  6. filtrationby filtration
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:1)

Sources & evidence

ORD record
ord-347b417325fe408abbecbd635706fc57
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Reaction notes

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