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

HRID 2243103노트

반응식

HRID 2243103 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8ec235f234744934b39064810feb0f7a
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674809B2

반응 노트

불러오는 중…