Hydrochloric Acid → HCID 18407191, compound

HRID 1016581Notes

Reaction equation

HRID 1016581 reaction equation
[C:1]([N:4]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31].Cl>CN(C)C=O>[C:1]([N:4]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:29][C:30]([O:32][CH3:33])=[O:31])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 18407204HCID 18407204, compound

Product 1

HCID 18407191HCID 18407191, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 666 mg of N-acetyl-N-(2-hydroxybenzyl)-2-phenoxyaniline in 10 ml of N,N-dimethylformamide was added 80 mg of 60% NaH/oil, followed by stirring at room temperature for 30 minutes. To this was added 0.3 ml of methyl bromoacetate, followed by stirring at room temperature for 30 minutes. The reaction solution was poured into 0.5 N hydrochloric acid and extracted with ethyl acetate. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give a crude N-acetyl-N-(2-methoxycarbonylmethoxybenzyl)-2-phenoxyaniline.

Workup

  1. stirringby stirring at room temperature 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 a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-142acaedd1024e15a33b27484c8197d7
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Reaction notes

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