Chlorosuccinimide → 29568-74-9

HRID 2407656Notes

Reaction equation

HRID 2407656 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[CH:12]=[N:13][OH:14]>CN(C)C=O.C(OC)(C)(C)C>[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([Cl:1])=[N:13][OH:14]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 96239o-Chlorobenzaldoxime

Product 1

HCID 380973329568-74-9Yield 99.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

N-Chlorosuccinimide (56.1 g) was added slowly to a 0° C. solution of the compound prepared in Example 4 (65.4 g) in N,N-dimethylformamide (1.2 L). The reaction was stirred at room temperature overnight and then diluted with ice water and methyl tert-butyl ether. The layers were separated and the aqueous phase was extracted once more with methyl tert-butyl ether. The organic phases were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated to obtain the title compound (79.5 g) having the following physical data.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted once more with methyl tert-butyl ether
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3548018002b54ae2a6844f1eda82bdc4
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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