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

HRID 429571

反応式

HRID 429571 の反応式
[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

参加物

8

反応物 3

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

生成物 1

HCID 193455-Amino-2-(trifluoromethyl)benzimidazole収率 80%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6422Trifluoroacetic acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-608787df50804d9f8286080e62b98460
出典データセット
uspto-grants-2001_11
特許番号
US06316637B1

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