Chlorosuccinimide → HCID 69269310, compound

HRID 751539Notes

Reaction equation

HRID 751539 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([C:11]2[C:12](=[O:27])[NH:13][C:14](=[O:26])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH3:25])[CH:17]=2)=[CH:4][CH:3]=1.[Cl:28]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([C:11]2[C:12](=[O:27])[NH:13][C:14](=[O:26])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH3:25])[C:17]=2[Cl:28])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 69269152HCID 69269152, compound

Product 1

HCID 69269310HCID 69269310, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 3-(4-hydroxybenzofur-7-yl)-4-(1-methyl-1H-indol-3-yl)pyrrole-2,5-dione (0.25 g, 0.70 mmol) in 50 mL chloroform under nitrogen. Add 0.093 g (0.70 mmol, 1 equiv) N-chloro succinimide and attach a reflux condenser. Heat to 50° C. and let go overnight. Let cool to room temperature, then extract with ethyl acetate versus water. Wash with brine, then dry over sodium sulfate. Filter and concentrate in vacuo. Purification by column chromatography (20% ethyl acetate: hexanes) yields 0.034 g (12%) product. High Res. Mass Spec (m/z): Calcd 393.0655 Found 393.0642.

Workup

  1. temperatureLet cool to room temperature
  2. extractionextract with ethyl acetate versus water
  3. washWash with brine
  4. dry with materialdry over sodium sulfate
  5. filtrationFilter
  6. concentrationconcentrate in vacuo
  7. customPurification by column chromatography (20% ethyl acetate: hexanes)

Sources & evidence

ORD record
ord-6c0e7ba742a3427cba15a15840788ee2
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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