Sodium Hydroxide → (E)-4-methyl-2-styryl-1H-benzimidazole

HRID 382548

反応式

HRID 382548 の反応式
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[C:10](O)(=O)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O>[CH3:9][C:3]1[C:2]2[N:1]=[C:10](/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 175932,3-DiaminotolueneHCID 444539Cinnamic Acid

生成物 1

HCID 22736633(E)-4-methyl-2-styryl-1H-benzimidazole収率 13%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
180 °C

実験手順

A mixture of 2,3-diaminotoluene (2.44 g, 20 mmol), (E)-cinnamic acid (2.96 g, 20 mmol) and polyphosphoric acid (10 g) was heated to 180° C. for 90 min. The hot mixture was poured into water (100 ml), basified with 50% aqueous solution of sodium hydroxide and extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (100 ml) and brine (100 ml), dried (magnesium sulfate) and concentrated to dryness. Purification by column chromatography (silica gel, 300 g; n-hexane/ethyl acetate (7/3)) yielded 0.61 g (13%) of the titled compound as red solids.

後処理

  1. extractionextracted with dichloromethane (3×100 ml)
  2. washThe combined extracts were washed with water (100 ml) and brine (100 ml)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated to dryness
  5. customPurification by column chromatography (silica gel, 300 g; n-hexane/ethyl acetate (7/3))

出典と根拠

ORDレコード
ord-c5fd9300e7a34cb499021e518bfba359
出典データセット
uspto-grants-2001_10
特許番号
US06310079B1

関連ノート

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