Azetidine → Benzimidazole

HRID 1945974Notes

Reaction equation

HRID 1945974 reaction equation
Cl[C:2]1[N:6](COCC[Si](C)(C)C)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.N1CCC1.CCN(C(C)C)C(C)C>C(O)C>[NH:3]1[C:4]2[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=2[N:6]=[CH:2]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 597528982-Chloro-1-[[2-(trimethylsilanyl)ethoxy]methyl]-benzimidazole

Product 1

HCID 5798Benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2-Chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole (0.5 g) was placed in a flask with azetidine (0.48 mL), Hunig's base (iPr2Net, 1.5 mL) in 1 mL of ethanol. The reaction was heated to 50° C. overnight and then concentrated to dryness to get 0.55 g of crude 2-(azetidin-1-yl)-1-(2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f80b3f18970240eaa31eab86969933e5
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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