Pyridine → N-hydroxybenzenecarboximidoyl chloride

HRID 2120851Notes

Reaction equation

HRID 2120851 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:16]N1C(=O)CCC1=O.[Na+].[Cl-]>C(Cl)(Cl)Cl>[Cl:16][C:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide

Product 1

HCID 2756315N-hydroxybenzenecarboximidoyl chlorideYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To benzaldehyde oxime (12.2 g, 0.1 mol) in chloroform was added catalytic amount of pyridine, followed by N-chlorosuccinimide (13.35 g, 0.1 mol) at room temperature. The reaction mixture was stirred for 1.5 h, then saturated aqueous NaCl was added. The organic phase was washed with saturated aqueous NaCl (twice) and dried with MgSO4. The solvent was removed under reduced pressure. 13.85 g α-chlorobenzaldehyde oxime was obtained. The yield was 87%.

Workup

  1. washThe organic phase was washed with saturated aqueous NaCl (twice) and
  2. dry with materialdried with MgSO4
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b7940cd39b45435c9b2d625235ac7f5f
Source dataset
uspto-grants-2004_02
Patent number
US06693108B2

Reaction notes

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