Sodium ethoxide → 2-(azetidin-1-yl)-1H-benzo[d]imidazole

HRID 1923155Notes

Reaction equation

HRID 1923155 reaction equation
[N:1]1([C:5]2[N:9](COCC[Si](C)(C)C)[C:8]3[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=3[N:6]=2)[CH2:4][CH2:3][CH2:2]1.[O-]CC.[Na+]>CN(C=O)C.O>[N:1]1([C:5]2[NH:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[N:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 596054842-(azetidin-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole

Product 1

HCID 596058832-(azetidin-1-yl)-1H-benzo[d]imidazoleYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Into a sealed vessel was placed crude 2-(azetidin-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H benzo[d]imidazole (0.55 g) and sodium ethoxide (1.2 g) in DMF (14 mL). The reacted was heated for 30 mins at 150° C. in an oil bath. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated to give 310 mg of 2-(azetidin-1-yl)-1H-benzo[d]imidazole as yellow solid.

Workup

  1. customInto a sealed vessel was placed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1dd1ec330bee443e89e83378d23c4ec9
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…