Water → N-hydroxybenzenecarboximidoyl chloride

HRID 2111669Notes

Reaction equation

HRID 2111669 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH:9](=[N:16][OH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>CN(C=O)C>[Cl:1][C:9](=[N:16][OH:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide

Product 1

HCID 2756315N-hydroxybenzenecarboximidoyl chlorideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-chlorosuccinimide (5.50 g, 41.3 mmol) was added in portions to a solution of benzaldehyde oxime (5.0 g, 41.3 mmol) in DMF (34 ml) such that the temperature did not rise above 35° C. The mixture was stirred at ambient temperature for 2 hours and then cooled with an ice bath. Water was added and the aqueous mixture extracted with ether. The organics were combined, washed with water and brine, dried (MgSO4) and the solvent removed by evaporation to give the title compound (6.43 g, 100%) as an oil. NMR (CDCl3): 7.4 (m, 3H), 7.8 (d, 2H), 8.9 (bs, 1H).

Workup

  1. customdid not rise above 35° C
  2. temperaturecooled with an ice bath
  3. extractionthe aqueous mixture extracted with ether
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-0793763dd9ac45379132c6ff853981b4
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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