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Sodium hydride → 3-[1-[3-(2-imidazolylthio)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione

HRID 345678
Notes
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Reaction equation

HRID 345678 reaction equation
[H-].[Na+].[SH:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[C:20](=[O:42])[NH:21][C:22](=[O:41])[C:23]=2[C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH2:33][CH2:34][CH2:35]OS(C)(=O)=O)[CH:25]=2)=[CH:11]1>CN(C=O)C>[NH:5]1[CH:6]=[CH:7][N:8]=[C:4]1[S:3][CH2:35][CH2:34][CH2:33][N:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]([C:23]2[C:22](=[O:41])[NH:21][C:20](=[O:42])[C:19]=2[C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]([CH3:9])[CH:11]=2)=[CH:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 151630513-(1-methyl-3-indolyl)-4-[1-[3-(methylsulphonyloxy)propyl]-3-indolyl]-1H-pyrrole-2,5-dioneHCID 178527877HCID 178527877, compound

Product 1

HCID 187803043-[1-[3-(2-imidazolylthio)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dioneYield 19.8%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

7 mg of a 80% dispersion of sodium hydride in mineral oil was added to a cooled solution of 23 mg of 2-mercaptoimidazole in 10 ml of DMF. The mixture was stirred for 0.5 hour while cooling. 100 mg of the product of Example 58 were added and the mixture was stirred for 2 hours while cooling. The mixture was then allowed to warm to room temperature and was stirred overnight. The solvents were removed under reduced pressure and the residue was chromatographed on silica gel with 10% methanol in dichloromethane to give 20 mg of 3-[1-[3-(2-imidazolylthio)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 130°-132° C.

Workup

  1. temperaturewhile cooling
  2. stirringthe mixture was stirred for 2 hours
  3. temperaturewhile cooling
  4. stirringwas stirred overnight
  5. customThe solvents were removed under reduced pressure
  6. customthe residue was chromatographed on silica gel with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-05321765110e44a9872c36ac99455001
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05057614

Reaction notes

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