Potassium Hydroxide → 4,5-dichloro-1-(naphthalen-2-ylmethyl)-1H-imidazole

HRID 922594노트

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HRID 922594 반응식
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].Br[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:6]=1[Cl:7]

참가 물질

5

반응물 3

HCID 14797Potassium Hydroxide2회HCID 703202-BromomethylnaphthaleneHCID 1400184,5-Dichloroimidazole

생성물 1

HCID 709820944,5-dichloro-1-(naphthalen-2-ylmethyl)-1H-imidazole수율 89.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
85 °C

실험 절차

4,5-dichloroimidazole (40.0 mmol, 5.479 g) and KOH (44.0 mmol, 2.469 g) were placed in a round bottom flask with 100 mL acetonitrile. The mixture was brought to reflux (85° C.) and stirred 1 h until KOH was consumed. 2-Bromomethylnapthalene (40.00 mmol, 8.844 g) was added and the solution was stirred at reflux for 17 hours. KBr was removed by vacuum filtration and the filtrate was collected. The volatiles were removed by rotary evaporation to give 4,5-dichloro-1-(naphthalen-2-ylmethyl)-1H-imidazole as a light brown solid. 4,5-dichloro-1-(naphthalen-2-ylmethyl)-1H-imidazole (18 mmol) was dissolved in acetonitrile (40 mL) in a round bottom flask. The solution was brought to reflux and iodomethane (5 mL) was added. The reaction was stirred at reflux for 20 h after which time it was cooled. The resulting white precipitate was collected by filtration and analyzed. Yield: 89.6% 1H NMR (300 MHz, d6-DMSO): δ 3.86 (s), 5.68 (s), 7.53-7.59 (m), 7.93-8.03 (m), 9.51 (s) ppm.

후처리

  1. customwas consumed
  2. temperatureat reflux for 17 hours
  3. customKBr was removed by vacuum filtration
  4. customthe filtrate was collected
  5. customThe volatiles were removed by rotary evaporation

출처 및 근거

ORD 기록
ord-f4a26f1b38d04f7bbabe98c68d2c87b7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278951B2

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