Dimethylformamide → 6-methyl-N-phenyl-N-pyridin-2-ylpyridin-2-amine

HRID 909857

反応式

HRID 909857 の反応式
[CH:1]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=[CH:3][CH:2]=1.[H-].[Na+].ClCC1N(C)[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2N=1.[CH3:28]N(C)C=O>>[CH3:28][C:12]1[N:13]=[C:8]([N:7]([C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:21]=2)[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=2)[CH:9]=[CH:10][CH:11]=1

参加物

5

反応物 4

HCID 6228Dimethylformamide2 回HCID 145472,2'-DipyridylamineHCID 24758Sodium hydrideHCID 2480442-(Chloromethyl)-1-methylbenzimidazole

生成物 1

HCID 666281216-methyl-N-phenyl-N-pyridin-2-ylpyridin-2-amine

実験手順

To a flask were added 1.1 g of 2,2′-dipyridylamine and 25 ml of N,N-dimethylformamide. To this mixture were added 0.32 g of 60% sodium hydride in mineral oil in small portions, and after stirring at 10 C for ten minutes, 1.2 g of 2-(chloromethyl)-1-methyl-1H-benzimidazole in 5 ml of N,N-dimethylformamide were added. The reaction mixture was stirred at 22 C for several hours, and then quenched with 40 ml water. The product was extracted with 50 ml ethyl acetate, and then extracted with 30 ml of 1M hydrochloric acid, and basified with 3M sodium hydroxide. Following extraction with 20 ml ethyl acetate, the product was purified by silica gel chromatography using 33% ethyl acetate, 62% hexane, and 5% methanol, resulting in an oil which crystallized on standing. After drying, 0.6 g of a yellow solid remained.

後処理

  1. stirringThe reaction mixture was stirred at 22 C for several hours
  2. customquenched with 40 ml water
  3. extractionThe product was extracted with 50 ml ethyl acetate
  4. extractionextracted with 30 ml of 1M hydrochloric acid
  5. extractionextraction with 20 ml ethyl acetate
  6. customthe product was purified by silica gel chromatography
  7. customresulting in an oil which
  8. customcrystallized
  9. customAfter drying

出典と根拠

ORDレコード
ord-21fe33ea2fb8446686e54fbd5293b23c
出典データセット
uspto-grants-2011_09
特許番号
US08018639B2

関連ノート

読み込み中…