1,4-Dichlorobenzene → Methyl 4-(5,6-dinitro-1H-benzimidazol-2-yl)benzoate

HRID 1414374노트

반응식

HRID 1414374 반응식
ClC([CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O-:11])=[O:10])=[CH:7][CH:6]=1)=O.[NH2:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:16]=1[NH2:27].[CH:28]1C(Cl)=CC=C(Cl)C=1>>[C:9]([C:8]1[CH:7]=[CH:6][C:5]([C:4]2[NH:14][C:15]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([N+:24]([O-:26])=[O:25])=[CH:17][C:16]=3[N:27]=2)=[CH:13][CH:12]=1)([O:11][CH3:28])=[O:10]

참가 물질

4

반응물 3

HCID 46851,4-DichlorobenzeneHCID 44419034,5-Dinitrobenzene-1,2-diamineHCID 21487225p-Chlorocarbonylmethylbenzoate

생성물 1

HCID 21487223Methyl 4-(5,6-dinitro-1H-benzimidazol-2-yl)benzoate수율 62%

실험 절차

To a solution containing 10 g (45.8 mmole) of p-chlorocarbonylmethylbenzoate dissolved in 100 ml of dichlorobenzene was added 3.0 g (15.3 mmole) of 1,2-diamino-4,5-dinitrobenzene. After heating the resulting mixture to reflux under nitrogen (frothing), it was maintained at that temperature for 2 hours. The solution was then allowed to cool in ice for one hour, and the precipitate that formed was filtered by suction, washed with benzene and air-dried. Recrystallization from tetrahydrofuran (THF)-n-propanol by distillation to a small volume in vacuo yielded 3.2 g (62%) of 2-[p-carbomethoxyphenyl]-5,6-dinitrobenzimidazole as light yellow needles, m.p. 239°-240°.

후처리

  1. temperatureAfter heating the resulting mixture
  2. temperatureto reflux under nitrogen (frothing)
  3. temperatureit was maintained at that temperature for 2 hours
  4. temperatureto cool in ice for one hour
  5. customthe precipitate that formed
  6. filtrationwas filtered by suction
  7. washwashed with benzene
  8. customair-dried
  9. customRecrystallization from tetrahydrofuran (THF)-n-propanol
  10. distillationby distillation to a small volume in vacuo

출처 및 근거

ORD 기록
ord-19f72e4b6ac44116a23c217314fb8352
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04001268

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