Chloroacetamide → 2-(4-Chlorophenyl)-1H-imidazo[4,5-b]pyridine-1-acetamide

HRID 623088

反応式

HRID 623088 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:18][C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)=[CH:6][CH:5]=1.Cl[CH2:20][C:21]([NH2:23])=[O:22]>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([CH2:20][C:21]([NH2:23])=[O:22])[C:12]3[C:13]([N:18]=2)=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 6580ChloroacetamideHCID 24758Sodium hydrideHCID 178477971HCID 178477971、化合物

生成物 1

HCID 143904392-(4-Chlorophenyl)-1H-imidazo[4,5-b]pyridine-1-acetamide収率 86%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Under nitrogen flow, sodium hydride (0.96 g, 0.0234 mole, 60% in oil) was washed with hexanes (~70 ml) and decanted. Dimethylformamide was added (100 ml) and the 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine (5.0 g, 0.022 mole) was added in portions. The reaction mixture was heated at 70°-85° C. for 11/2 hours. Chloroacetamide (2.06 g, 0.022 mole) was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was added to water (~600 ml) and the precipitate was collected by filtration, washed with water, and dried under high vacuum overnight at 50° C. NMR indicated a 14% yield of the isomer: 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetamide and an 86% yield of the title compound. The solid was dissolved in pyridine, filtered, and diluted with water to produce crystalline product with refrigeration. The solid was collected by filtration, washed with water and dried under high vacuum at 90° C. overnight to give 2.3 g (36.5%) of the title compound, mp 280°-283° C. with decomposition.

後処理

  1. customdecanted
  2. additionDimethylformamide was added (100 ml)
  3. temperatureThe reaction mixture was heated at 70°-85° C. for 11/2 hours
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. customdried under high vacuum overnight at 50° C

出典と根拠

ORDレコード
ord-c348de95f9de4e86aebccd13d8bb023e
出典データセット
uspto-grants-1988_09
特許番号
US04772600

関連ノート

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