Sodium hydride → HCID 68438048, compound

HRID 1297494Notes

Reaction equation

HRID 1297494 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[C:12]([N+:16]([O-:18])=[O:17])=[CH:13][NH:14][CH:15]=1.BrCCC[C:23]1[CH:33]=[CH:32][CH:31]=[C:25]2[C:26]([NH:28][C:29](=[O:30])[C:24]=12)=[O:27].[CH2:34](Cl)Cl.[C:37](#N)[CH3:38]>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[C:12]([N+:16]([O-:18])=[O:17])=[C:13]([CH2:34][CH2:37][CH2:38][N:28]2[C:26](=[O:27])[C:25]3[CH:31]=[CH:32][CH:33]=[CH:23][C:24]=3[C:29]2=[O:30])[NH:14][CH:15]=1

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 470430HCID 470430, compoundHCID 21877088Acetonitrile methylene chlorideHCID 21958088Bromopropylphthalimide

Product 1

HCID 68438048HCID 68438048, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

The NaH (1.2 eq) was added to a dry flask under argon. To NaH suspended in DMF, was added a solution of 4-(2,4-dichlorophenyl)-3-nitropyrrole (1 eq) in DMF with stirring at RT. After the evolution of gas bubbles had stopped, the reaction stirred for an additional 15 min at which time a solution of 3-bromopropyl phthalimide (1.1 eq) in DMF was added to the yellow-brown solution. After 2 hours, the clear brown reaction was complete (determination by TLC: CH2Cl2/acetonitrile (95:5 v/v), the UV active product was at Rf=0.5). Upon completion, the reaction was quenched with half sat. aq. NH4Cl (added slowly to avoid strong gas evolution and exotherm). EtOAc was added, and after shaking the ivory colored precipitate which formed during the quench was collected by filtration. The organic layer was washed with water, brine, dried (Na2SO4), filtered, and concentrated to give the desired product as an ivory solid. Both portions of product were combined to afford (−94% yield) 95% pure 2-{3-[4-(2,4-dichlorophenyl)-3-nitropyrrolyl]propyl}benzo[c]azoline-1,3-dione (4), which was used without further purification (LC/MS m/z 445.3 MH+).

Workup

  1. additionwas added to the yellow-brown solution
  2. customthe clear brown reaction
  3. customUpon completion, the reaction was quenched with half sat. aq. NH4Cl (
  4. additionadded slowly
  5. additionEtOAc was added
  6. stirringafter shaking the ivory colored precipitate which
  7. customformed during the quench
  8. filtrationwas collected by filtration
  9. washThe organic layer was washed with water, brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-7b255e23b5ac4756b82f066977b82b7c
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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