Water → HCID 18407216, compound

HRID 2271201Notes

Reaction equation

HRID 2271201 reaction equation
Cl[CH2:2][C:3]([N:5]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].[N-:28]=[N+:29]=[N-:30].[Na+].O>CN(C)C=O>[N:28]([CH2:2][C:3]([N:5]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4])=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 18407214HCID 18407214, compound

Product 1

HCID 18407216HCID 18407216, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.51 g of N-chloroacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline synthesized in the same manner as in Example 1 and 770 mg of sodium azide in 10 ml of dimethylformamide was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. 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=1:4) to give 1.55 g of N-azidoacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline as an oil.

Workup

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

Sources & evidence

ORD record
ord-96b271e870134ad6b3b16857f4e54662
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

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