HCID 4447362、化合物 → 3-(1H-benzimidazol-2-yl)-4-chloroaniline

HRID 1803831ノート

反応式

HRID 1803831 の反応式
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O)=O>C1(C)C=CC=CC=1.C(O)(=O)C.[Fe]>[NH:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:13]=[C:4]1[C:3]1[CH:16]=[C:17]([NH2:20])[CH:18]=[CH:19][C:2]=1[Cl:1]

参加物

5

反応物 1

HCID 4447362HCID 4447362、化合物

生成物 1

HCID 2788313-(1H-benzimidazol-2-yl)-4-chloroaniline収率 49.7%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒

反応条件

温度
125 °C

実験手順

Iron powder (15.42 g, 280 mmol) was added to a solution of amide 1 (15.00 g, 46.7 mmol) in toluene (125 ml) and acetic acid (60 ml). The mixture was heated at 125° C. for about 1 h (completion of the reaction was monitored by LCMS) and the resulting crude mixture was filtered through a cotton wool plug (to remove iron particles). The crude solution was evaporated to dryness, diluted with EtOAc, washed with saturated NaHCO3 then brine, dried over MgSO4, filtered, and concentrated at reduced pressure. The resulting brown solid was re-dissolved in CH2Cl2 and few drops of hexane were added to form a solid which was isolated by filtration to give 2 (5.66 g, 42%) as a beige solid: 1H NMR (CD3OD) δ 7.64 (broad s, 2H), 7.30-7.26 (m, 3H), 7.13 (app d, 1H), 6.84 (dd, 1H); MS (ES, positive mode): 244 [M++1].

後処理

  1. filtrationwas filtered through a cotton wool plug (to remove iron particles)
  2. customThe crude solution was evaporated to dryness
  3. additiondiluted with EtOAc
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. dissolutionThe resulting brown solid was re-dissolved in CH2Cl2
  9. additionfew drops of hexane were added
  10. customto form a solid which
  11. customwas isolated by filtration

出典と根拠

ORDレコード
ord-f6e20cab3e76452087cf961cd47ad9f9
出典データセット
uspto-grants-2013_01
特許番号
US08354397B2

反応ノート

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