Dichloromethane → 2-(1-methyl-1H-indol-3-yl)-3-phenyl-N-methylmaleimide

HRID 1168658

Reaction equation

HRID 1168658 reaction equation
C(Cl)Cl.[CH3:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:16](=[O:17])[C:15]=2Br)=[CH:6]1.ClS(O)(=O)=O.CC(C)C(N)=O.[CH3:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C(#N)C>[CH3:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:16](=[O:17])[C:15]=2[C:36]2[CH:35]=[CH:34][CH:39]=[CH:38][CH:37]=2)=[CH:6]1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 8058HexaneHCID 24638Chlorosulfonic acidHCID 68424IsobutyramideHCID 98184713-Bromo-1-methyl-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

Product 1

HCID 178436842-(1-methyl-1H-indol-3-yl)-3-phenyl-N-methylmaleimide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into methylene chloride (83 ml) was dissolved the resultant IM-4 (25 g, 80.5 mmol) obtained as described above, and to this was added dropwise chlorosulfonic acid (8.3 ml) at room temperature. After this mixture was stirred for an hour at room temperature, to the reaction system were added dropwise at a low speed dimethylacetoamide (90 ml)/acetonitrile (45 ml). To this was added dropwise oxy-salt phosphor (15 ml) while being heated and refluxed. After this mixture was heated and refluxed for an hour, hexane (150 ml) was added, then, the mixture was stirred and stood still, and thereafter, the upper layer of hexane was separated and concentrated. The concentrated substances were refined with silica gel column chromatography to obtain 21 g of IM-5.

Workup

  1. customobtained
  2. additionTo this was added dropwise oxy-salt phosphor (15 ml)
  3. temperaturewhile being heated
  4. temperaturerefluxed
  5. temperatureAfter this mixture was heated
  6. temperaturerefluxed for an hour
  7. stirringthe mixture was stirred
  8. customthe upper layer of hexane was separated
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bb987a43e59f48e0a2f68bba9e46ebb8
Source dataset
uspto-grants-2003_09
Patent number
US06627099B2

Linked notes

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