Chlorosuccinimide → HCID 66990431, compound

HRID 2407822Notes

Reaction equation

HRID 2407822 reaction equation
[NH2:1][C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[N:4][C:5]([O:8][CH2:9][CH3:10])=[CH:6][CH:7]=1.[Cl:15]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[N:4][C:5]([O:8][CH2:9][CH3:10])=[CH:6][C:7]=1[Cl:15]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 66989945HCID 66989945, compound

Product 1

HCID 66990431HCID 66990431, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of the compound prepared in Example 426 (0.048 g) in N,N-dimethylformamide (1.2 mL) was added N-chlorosuccinimide (0.0343 g). The resulting mixture was heated at 80° C. for 18 hours. The solvent was evaporated and the residue dissolved in dichloromethane and purified by column chromatography on silica gel (20% ethyl acetate in hexanes) to obtain the title compound (0.003 g) having the following physical data.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. custompurified by column chromatography on silica gel (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-44ad355e3a864c7194dc4be2063ac3cf
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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