Chlorosuccinimide → HCID 10565174, compound

HRID 1736097Notes

Reaction equation

HRID 1736097 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[C:5]([Cl:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 10422310HCID 10422310, compound

Product 1

HCID 10565174HCID 10565174, compoundYield 12%

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, 1.59 g (11.9 mmol) of N-chlorosuccinimide was added and the mixture was stirred under heating at reflux for 5 hours. The reaction solution was extracted with ethyl acetate, and 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 0.61 g (27%) of crude product. Further recrystallization from chloroform/methanol afforded 266 mg (12%) of Compound 2.

Workup

  1. temperatureunder heating
  2. temperatureat reflux for 5 hours
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washthe extract was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform: acetone=4:1)
  8. customto give 0.61 g (27%) of crude product
  9. customFurther recrystallization from chloroform/methanol

Sources & evidence

ORD record
ord-fbf030ce77dc49968aa6f01a4581755a
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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