Hydrogen Peroxide → HCID 58541889、化合物

HRID 1966725ノート

反応式

HRID 1966725 の反応式
[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]#[N:12])=[N:8][C:4]=2[CH:3]=1.[OH-:23].[NH4+].OO>CO>[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:17]([CH3:18])([CH3:19])[CH3:20])[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]([NH2:12])=[O:23])=[N:8][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 58542011HCID 58542011、化合物

生成物 1

HCID 58541889HCID 58541889、化合物収率 84%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a round bottom flask is added 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzonitrile (1800 mg, 5.08 mmol) in MeOH (40 mL), followed by the addition of ammonium hydroxide (20 mL) and hydrogen peroxide (10 mL) (30% in water). The reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with EtOAc, washed with water then brine, dried under Na2SO4, filtered and concentrated. The residue is loaded onto a silica gel column. The column is eluted with 0-4% MeOH/CH2Cl2. The product fractions are collected and concentrated to afford 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzamide (1590 mg, 84%) as a light brown solid. LCMS (ESMS): m/z 372.46, 374.35 (M++1)

後処理

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionThe residue is diluted with EtOAc
  3. washwashed with water
  4. dry with materialbrine, dried under Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe column is eluted with 0-4% MeOH/CH2Cl2
  8. customThe product fractions are collected
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-70def71dad41472a8face902f5ba2d4a
出典データセット
uspto-grants-2013_04
特許番号
US08420655B2

反応ノート

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