Water → 3-(2,6-dichlorophenyl)-N-hydroxypropanimidoyl chloride

HRID 1693663Notes

Reaction equation

HRID 1693663 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][CH:11]=[N:12][OH:13].[Cl:14]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]([Cl:14])=[N:12][OH:13]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 722650173-(2,6-Dichlorophenyl)propanal oxime

Product 1

HCID 722650183-(2,6-dichlorophenyl)-N-hydroxypropanimidoyl chlorideYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2,6-dichlorophenyl)propanal oxime (1.05 g, 4.82 mmol) in dimethylformamide (3.8 mL) was stirred as N-chlorosuccinimide (0.64 g, 4.82 mmol) was added. The resulting solution was allowed to stir for one hour. The solution was poured into water and extracted with ether. The organic layer was washed with brine, dried with magnesium sulfate, filtered and concentrated to yield the title compound (1.05 g, 86%). 1H NMR (DMSO-d6): 11.67 (s, 1H), 7.45 (d, J=8 Hz, 2H), 7.28 (t, J=8 Hz, 1H), 3.17-3.13 (m, 2H), 2.68-2.64 (m, 2H).

Workup

  1. additionwas added
  2. extractionextracted with ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-67c2376046ba44dfbef6deb3baaae7f8
Source dataset
uspto-grants-2012_04
Patent number
US08158665B2

Reaction notes

Loading…