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

HRID 869549

Reaction equation

HRID 869549 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[NH:11]1[CH2:14][CH2:13][CH2:12]1.O>C1COCC1.O>[N:11]1([C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=2)[CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 962WaterHCID 10422AzetidineHCID 785722-Chlorobenzimidazole

Product 1

HCID 596058832-(azetidin-1-yl)-1H-benzo[d]imidazoleYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
180 °C

Procedure

[step 1] Commercially available 2-chloro-1H-benzo[d]imidazole (200 mg, 1.31 mmol) was dissolved in THF (1.9 mL), azetidine (0.27 mL, 3.93 mmol) and water (0.27 mL, 0.015 mmol) were added, and the mixture was stirred with heating in an Emrys Optimizer microwave synthesizer at 180° C. for 3 hr. Water was added to the mixture, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-90/10 v/v) to give 2-(azetidin-1-yl)-1H-benzo[d]imidazole (40 mg, 18%).

Workup

  1. extractionthe mixture was extracted 3 times with chloroform
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-90/10 v/v)

Sources & evidence

ORD record
ord-35971092043a43c9addacb1c9bf40e86
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Linked notes

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