Chlorosuccinimide → 2,6-Dichloro-benzaldehyde chloro-oxime

HRID 1689818Notes

Reaction equation

HRID 1689818 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:11]=1[CH:12]=[N:13][OH:14]>CN(C=O)C>[Cl:1][O:14][N:13]=[CH:12][C:11]1[C:10]([Cl:9])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 91328Benzaldehyde, 2,6-dichloro-, oxime

Product 1

HCID 866424822,6-Dichloro-benzaldehyde chloro-oximeYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

N-Chlorosuccinimide (1162 g, 8.53 mol) in DMF (4.5 L) is added dropwise over a solution of 2,6-dichloro-benzaldehyde oxime (1621.78 g, 8.53 mol) in DMF (5.3 L) heated at 40° C. (addition is complete in about 6 hours). The mixture is stirred for 1 h at that temperature. The reaction is cooled at room temperature, poured onto H2O (30 L) at 0° C., and extracted with MTBE (36 L). The organic layer is washed with brine, dried over Na2SO4, filtered and evaporated to dryness (at 30° C.). The crude, as a solid-oil, is triturated in 1 L of hexane and the solid formed is filtered and dried under vacuum to obtain the desired compound (1440.9 g, 75% yield). MS (m/e): 224 (M+1)

Workup

  1. addition(addition is complete in about 6 hours)
  2. temperatureThe reaction is cooled at room temperature
  3. additionpoured onto H2O (30 L) at 0° C.
  4. extractionextracted with MTBE (36 L)
  5. washThe organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness (at 30° C.)
  9. customThe crude, as a solid-oil, is triturated in 1 L of hexane
  10. customthe solid formed
  11. filtrationis filtered
  12. customdried under vacuum

Sources & evidence

ORD record
ord-50395c96830045fca1c1f2f10d911c0e
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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