Benzene → HCID 18779224, compound

HRID 240300Notes

Reaction equation

HRID 240300 reaction equation
S([O-])(=O)(=O)C.[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.[K].[I-].[Na+].[CH3:20][N:21]([CH3:24])[CH:22]=O.[CH:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[C:20]([N:21]1[CH:24]=[C:9]([CH2:8][CH2:7][CH2:6][N:10]2[C:6](=[O:16])[C:7]3=[CH:15][CH:14]=[CH:13][CH:12]=[C:8]3[C:9]2=[O:11])[N:10]=[CH:22]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 241BenzeneHCID 5238Sodium IodideHCID 6228DimethylformamideHCID 85257MethanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 18779224HCID 18779224, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the above mesylate (30.0 g, 67 mmol), potassium phtalimide (18.0 g, 100 mmol), sodium iodide (4.0 g, 26.7 mmol) and dimethylformamide (200 mL) was stirred overnight at ambient temperature and then treated with water (2 L) and benzene (2 L). The organic phase was dried over anhydrous magnesium sulfate, filtered and solvent evaporated giving a residue, which was recrystallised from benzene yielding 1-trityl-4-(3-phtalimidopropyl)imidazole as white solid.

Workup

  1. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. customsolvent evaporated
  4. customgiving a residue, which
  5. customwas recrystallised from benzene

Sources & evidence

ORD record
ord-e923093d7b2847fc919fc73018ae9cbd
Source dataset
uspto-grants-2014_02
Patent number
US08648041B2

Reaction notes

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