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Methanol → 2-[4-(4,5-Diphenylimidazol-1-yl)-butyl]-isoindol-1,3-dione

HRID 2251943
Notes
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Reaction equation

HRID 2251943 reaction equation
[H-].[Na+].[C:3]1([C:9]2[N:10]=[CH:11][NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].CO>CN(C=O)C>[C:3]1([C:9]2[N:10]=[CH:11][N:12]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[C:29](=[O:30])[C:28]4[C:27](=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:26]3=[O:35])[C:13]=2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 695884,5-DiphenylimidazoleHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 102239732-[4-(4,5-Diphenylimidazol-1-yl)-butyl]-isoindol-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

1.7 g (70.8 mmol) sodium hydride are placed in 130 ml DMF and 1.0 g (54.5 mmol) 4,5-diphenylimidazole are added under cooling. The suspension is stirred for four hours at RT and, subsequently, 15.4 g (54.5 mmol) N-(4-bromobutyl)-phthalimide dissolved in DMF is added dropwise under cooling. After complete addition, the reaction mixture is stirred for 12 hours at RT, 18 ml methanol are carefully added dropwise and the suspension is filtered. The filtrate is concentrated under vacuum and the residue is distributed between 500 ml chloroform and 170 ml water. The organic phase is dried over sodium sulfate and evaporated under vacuum until dry dried. The residue is purified by chromatography on silica gel with CHCl3/CH3OH (95/5) and subsequently crystallized from methanol: Yield 16.5 g (72%).

Workup

  1. temperatureunder cooling
  2. additionis added dropwise
  3. temperatureunder cooling
  4. additionAfter complete addition
  5. stirringthe reaction mixture is stirred for 12 hours at RT
  6. filtrationthe suspension is filtered
  7. concentrationThe filtrate is concentrated under vacuum
  8. dry with materialThe organic phase is dried over sodium sulfate
  9. customevaporated under vacuum
  10. customuntil dry
  11. customdried
  12. customThe residue is purified by chromatography on silica gel with CHCl3/CH3OH (95/5)
  13. customsubsequently crystallized from methanol

Sources & evidence

ORD record
ord-ffbce5063ecf45bd848d1555cf4507b8
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07320993B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes