Chlorosuccinimide → HCID 10660913, compound

HRID 1736096Notes

Reaction equation

HRID 1736096 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:19])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:20]N1C(=O)CCC1=O>O1CCOCC1>[NH2:1][C:2]1[C:7]2[C:8](=[O:19])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[O:11][C:6]=2[CH:5]=[CH:4][C:3]=1[Cl:20]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 10422310HCID 10422310, compound

Product 1

HCID 10660913HCID 10660913, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.0 g (7.93 mmol) of 5-amino-2-(4-aminophenyl)-4H-1-benzopyran-4-one (EP-A-374789) was dissolved in 50 ml of dioxane, 1.06 g (7.93 mmol) of N-chlorosuccinimide was added and the mixture was stirred under heating at reflux for 19 hours. The reaction solution was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:acetone=4:1) to give 710 mg (31%) of crude product. Further recrystallization from chloroform/methanol afforded 415 mg (18%) of Compound 1.

Workup

  1. temperatureunder heating
  2. temperatureat reflux for 19 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:acetone=4:1)
  9. customto give 710 mg (31%) of crude product
  10. customFurther recrystallization from chloroform/methanol

Sources & evidence

ORD record
ord-c69c749390304525a4e6eee41f52f20a
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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