Chlorosuccinimide → HCID 21938656, compound

HRID 1596640Notes

Reaction equation

HRID 1596640 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:16]N1C(=O)CCC1=O>FC1C=CC=CC=1>[Cl:16][C:5]1[CH:6]=[C:7]([O:9][C:10](=[O:15])[C:11]([CH3:12])([CH3:14])[CH3:13])[CH:8]=[C:2]([F:1])[C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 21938659HCID 21938659, compound

Product 1

HCID 21938656HCID 21938656, compound

Reagents, catalysts & solvents 1

HCID 10008FluorobenzeneSolvent

Procedure

A mixture of 7.3 g (0.035 mol) of 2-fluoro-4-pivaloyloxyaniline and 5.1 g (0.038 mol) of N-chlorosuccinimide in 50 ml of fluorobenzene is heated to reflux under a nitrogen atmosphere for two hours. After cooling to room temperature, the solvent is removed, water is added, and the mixture is extracted with ethyl acetate. The organic layer is washed with 1 N sodium hydroxide, and saturated brine, and dried over magnesium sulfate. Filtration and removal of the solvents gives a residue which is purified by silica gel chromatography (20% ethyl acetate/hexane) to give 2-chloro-4-pivaloyloxy-6-fluoroaniline. Conversion of 2-chloro-4-pivaloyloxy-6-fluoroaniline to 5-methyl-2-(2′-chloro-4′-hydroxy-6′-fluoroanilino)phenylacetic acid is carried out in a manner similar to that described in Example 1, the pivaloyl group being hydrolyzed in the last step along with the dimethylamide to give the final product.

Workup

  1. temperatureis heated
  2. temperatureto reflux under a nitrogen atmosphere for two hours
  3. customthe solvent is removed
  4. additionwater is added
  5. extractionthe mixture is extracted with ethyl acetate
  6. washThe organic layer is washed with 1 N sodium hydroxide, and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and removal of the solvents
  9. customgives a residue which
  10. customis purified by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7c6410a026824f60966ac8a42b8463d1
Source dataset
uspto-grants-2001_09
Patent number
US06291523B1

Reaction notes

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