p-Toluenesulfonic acid → 2-(2-Methylphenyl)-5-nitrobenzimidazole

HRID 2243103ノート

反応式

HRID 2243103 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=O.[NH2:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[NH2:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]1[NH:11][C:12]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=2[N:14]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 702762-Methylbenzoyl chlorideHCID 51117914-Nitro-1,2-phenylenediamine

生成物 1

HCID 232750332-(2-Methylphenyl)-5-nitrobenzimidazole

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

2-Methylbenzoyl chloride (4.1 g, 0.027 mol) is added to 2-amino-4-nitroaniline (4 g, 0.025 mol) in toluene (100 ml), and the mixture is refluxed for 24 hours. para-Toluenesulfonic acid (1.0 g) is added, the mixture is refluxed for 36 hours and concentrated, and the residue is taken up in ethyl acetate. The solution is washed with NaHCO3 and then with water. The resulting solution is dried and concentrated, and the solid obtained is recrystallized from isopropyl ether. Yield: 3.1 g (48%); Rf (7/3 toluene/ethyl acetate): 0.58; 1H-NMR (d6-DMSO): 8.5 (d, 1H); 8.1 (dd, 1H); 7.7 (m, 2H); 7.4 (m, 3H); 2.6 (s, 3H).

後処理

  1. temperaturethe mixture is refluxed for 24 hours
  2. temperaturethe mixture is refluxed for 36 hours
  3. concentrationconcentrated
  4. washThe solution is washed with NaHCO3
  5. customThe resulting solution is dried
  6. concentrationconcentrated
  7. customthe solid obtained
  8. customis recrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-8ec235f234744934b39064810feb0f7a
出典データセット
uspto-grants-2010_03
特許番号
US07674809B2

反応ノート

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