Water → N-acetyl-N-(2-isopropoxybenzyl)-2-phenoxyaniline

HRID 2271191Notes

Reaction equation

HRID 2271191 reaction equation
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].O>O1CCCC1>[C:33]([N:8]([CH2:7][C:6]1[CH:22]=[CH:23][CH:24]=[CH:25][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18407213N-(2-isopropoxybenzyl)-2-phenoxyaniline

Product 1

HCID 13005995N-acetyl-N-(2-isopropoxybenzyl)-2-phenoxyaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran were dissolved 2.65 g of N-(2-isopropoxybenzyl)-2-phenoxyaniline and 1.5 ml of triethylamine, and then 0.8 ml of acetyl chloride was added dropwise to the solution with stirring, followed by stirring for 30 minutes. The reaction mixture was poured to water and extracted with ethyl acetate, and the extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and then with a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:4) to give 2.92 g of N-acetyl-N-(2-isopropoxybenzyl)-2-phenoxyaniline as an oil.

Workup

  1. stirringby stirring for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with 0.5 N hydrochloric acid
  4. dry with materiala saturated aqueous sodium bicarbonate solution and then with a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  5. customAfter removal of the drying agent
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:4)

Sources & evidence

ORD record
ord-12718e09ac6a4521a786533b26484509
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

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