Water → N-Chloro-4-methoxybenzamide

HRID 1742523Notes

Reaction equation

HRID 1742523 reaction equation
[CH3:1][O:2][C:3]1C=CC(C=NO)=[CH:5][CH:4]=1.[Cl:12][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=O.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:16]([C:17]([NH:13][Cl:12])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 94712N-[(4-Methoxyphenyl)methylidene]hydroxylamine

Product 1

HCID 21579386N-Chloro-4-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved in 65 ml of dimethylformamide were 6.5 g (43 mmol) of 4-methoxybenzaldoxime, followed by the gradual addition of 6.3 g (47 mmol) of N-chlorosuccinimide at room temperature. After the resultant mixture was stirred for 3 hours, 300 ml of water were added to the reaction mixture. The mixture thus formed was extracted with ethyl ether. The ether layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off, whereby 4-methoxybenzhydroxamic acid chloride was obtained. Analytical results of the compound obtained: Yield: 7.98 g (100%).

Workup

  1. customThe mixture thus formed
  2. extractionwas extracted with ethyl ether
  3. washThe ether layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ed12404da74e45f1b25d29872765c8f2
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Reaction notes

Loading…