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

HRID 869549

반응식

HRID 869549 반응식
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

참가 물질

6

반응물 3

HCID 962WaterHCID 10422AzetidineHCID 785722-Chlorobenzimidazole

생성물 1

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

시약·촉매·용매 2

HCID 962Water촉매HCID 8028Tetrahydrofuran용매

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온도
180 °C

실험 절차

[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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-35971092043a43c9addacb1c9bf40e86
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969345B2

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