Chlorosuccinimide → HCID 86616900, compound

HRID 606124Notes

Reaction equation

HRID 606124 reaction equation
[Cl:1]N1C(=O)CCC1=O.[O:9]=[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]1[CH2:20][CH:21]=[N:22][OH:23]>CN(C=O)C.C(OCC)(=O)C>[O:19]=[C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=[O:9])[N:11]1[CH2:20][C:21]([Cl:1])=[N:22][OH:23]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 86616899HCID 86616899, compound

Product 1

HCID 86616900HCID 86616900, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

N-Chlorosuccinimide (8.50 g, 63.7 mmol) was added to a solution of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanal oxime (13.0 g, 63.7 mmol) in DMF (100 mL), and the solution was heated at 50° C. gently for two hours and allowed to cool to room temperature. The solution was diluted with ethyl acetate and washed three times with water and once with brine, dried over magnesium sulfate, filtered, and concentrated to provide 15.0 g of 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-hydroxyethanimidoyl chloride as a pale yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. washwashed three times with water
  3. dry with materialonce with brine, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-62a3922ad8834d729c1e1d6bc0ad9b14
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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