Water → 2-(6-Methyl-2-pyridyl)-1-(6-(phthalimido)hexyl)imidazole

HRID 72063Notes

Reaction equation

HRID 72063 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36].O>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]3[C:30](=[O:31])[C:29]4=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]4[C:27]3=[O:36])[CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 141120N-(6-Bromohexyl)phthalimideHCID 181727792-(1H-imidazol-2-yl)-6-methylpyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 181727772-(6-Methyl-2-pyridyl)-1-(6-(phthalimido)hexyl)imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(6-Methyl-2-pyridyl)imidazole (2.16 g) and sodium t-butoxide (1.57 g) in 50 mL dry DMF was added N-(6-bromohexyl)phthalimide (4.72 g). The resulting solution was stirred at room temperature for 3 h and then at 60° C. for 3.5 h. The solution was poured into H2O (80 mL) and then extracted three times with EtOAc (3×100 mL). The combined EtOAc extract was dried with anhydrous Na2SO4, and then evaporated to dryness. The product was purified by a silica gel column using EtOAc as the eluent. Yield: about 4.2 g.

Workup

  1. waitat 60° C. for 3.5 h
  2. extractionextracted three times with EtOAc (3×100 mL)
  3. extractionThe combined EtOAc extract
  4. dry with materialwas dried with anhydrous Na2SO4
  5. customevaporated to dryness
  6. customThe product was purified by a silica gel column

Sources & evidence

ORD record
ord-71b6e99b7bb2445282e3da4f6c2a4ae4
Source dataset
uspto-grants-2014_09
Patent number
US08828204B2

Reaction notes

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