Morpholine → 3-bromo-1-methyl-4-morpholino-1H-pyrrole-2,5-dione

HRID 1776317Notes

Reaction equation

HRID 1776317 reaction equation
Br[C:2]1[C:3]([N:5]([CH3:10])[C:6](=[O:9])[C:7]=1[Br:8])=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CN(C=O)C>[Br:8][C:7]1[C:6](=[O:9])[N:5]([CH3:10])[C:3](=[O:4])[C:2]=1[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 181552,3-Dibromo-N-methylmaleimide

Product 1

HCID 593547463-bromo-1-methyl-4-morpholino-1H-pyrrole-2,5-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature, stirred solution of 2,3-dibromo-N-methylmaleimide (1 g, 0.004 mol) in DMF (10 mL) was added Cs2CO3(1.34 g, 0.004 mol) followed by morpholine (360 mg, 0.004 mol) under N2 atmosphere. The reaction mixture was then stirred for 30 minutes, quenched with ice water, and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 3-bromo-1-methyl-4-morpholino-1H-pyrrole-2,5-dione (0.87 g, 85%) as a solid.

Workup

  1. customquenched with ice water
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68bbf37765fd4b66a1dfd8467cde2b06
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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