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

HRID 922594ノート

反応式

HRID 922594 の反応式
[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]

参加物

5

反応物 3

HCID 14797Potassium Hydroxide2 回HCID 703202-BromomethylnaphthaleneHCID 1400184,5-Dichloroimidazole

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4a26f1b38d04f7bbabe98c68d2c87b7
出典データセット
uspto-grants-2016_03
特許番号
US09278951B2

反応ノート

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