6-Nitro-2-(trifluoromethyl)-1H-benzimidazole → 5-Amino-2-(trifluoromethyl)benzimidazole

HRID 2299149

반응식

HRID 2299149 반응식
[N+](C1C=CC(N)=C(N)C=1)([O-])=O.[F:12][C:13]([F:27])([F:26])[C:14]1[NH:15][C:16]2[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:17]=2[N:18]=1.[N+](C1NC2C=CC=CC=2N=1)([O-])=O>FC(F)(F)C(O)=O.CCOC(C)=O.CO.[Pd]>[F:27][C:13]([F:12])([F:26])[C:14]1[NH:15][C:16]2[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:17]=2[N:18]=1

참가 물질

8

반응물 3

HCID 675956-Nitro-2-(trifluoromethyl)-1H-benzimidazoleHCID 972342-Nitro-1H-benzimidazoleHCID 51117914-Nitro-1,2-phenylenediamine

생성물 1

HCID 193455-Amino-2-(trifluoromethyl)benzimidazole수율 80%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6422Trifluoroacetic acid용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-nitro-1,2-phenylenediamine (3.0 g, 20 mmol) in 15 ml of trifluoroacetic acid was stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo to yield a oily residue, which was dissolved in 100 ml of EtOAc and washed with aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated in vacuo to provide an oil which was characterized as 2-trifluoromethyl-5-nitrobenzimidazole and subjected to the following reaction without further purification. The nitrobenzimidazole and 500 mg of 10% Pd-C were dissolved in 100 ml of MeOH and stirred for 12 h under H2. The reaction mixture was filtered and concentrated in vacuo, yielding 3.2 g (16 mmol, 80%) of the desired product.

후처리

  1. temperatureat reflux for 12 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto yield a oily residue, which
  4. washwashed with aqueous NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto provide an oil which
  8. customsubjected to the following reaction without further purification
  9. filtrationThe reaction mixture was filtered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ab4002b281cb41b58dbf56acf2212ce5
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495583B1

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