Formic Acid → 7-Chloro-1H-benzo[d]imidazol-5-amine

HRID 429580

反応式

HRID 429580 の反応式
ClC1C(N)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1.C(O)=O.[Cl:18][C:19]1[C:27]2[NH:26][CH:25]=[N:24][C:23]=2[CH:22]=[C:21]([NH:28]C=O)[CH:20]=1.C(N)=O>C(OC(=O)C)(=O)C.Cl.[Pd].CCO>[Cl:18][C:19]1[C:27]2[NH:26][CH:25]=[N:24][C:23]=2[CH:22]=[C:21]([NH2:28])[CH:20]=1

参加物

9

反応物 4

HCID 284Formic AcidHCID 713FormamideHCID 190526-Chloro-2,4-dinitroanilineHCID 178522168HCID 178522168、化合物

生成物 1

HCID 1785076737-Chloro-1H-benzo[d]imidazol-5-amine

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 7918Acetic Anhydride溶媒

実験手順

Methanolic solution of 6-chloro-2,4-dinitroaniline (2.4 g, 11 mmol) was stirred overnight with 100 mg of 10% Pd/C under H2. Reaction mixture was filtered and concentrated in vacuo to provide an oil which was dissolved in 10 ml of acetic anhydride and 10 ml of formic acid and stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo, yielding a brown oil which was characterized as 4-chloro-6-foramidylbenzimidazole in NMR analysis. The formamide was dissolved in 20 ml of HCl sat'd EtOH and stirred for 3h at 25° C. The reaction mixture was purified in column chromatography (5% MeOH/EtOAc) to provide 0.89 g (5.3 mmol, 48% overall) of the desired product.

後処理

  1. customReaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated in vacuo
  4. customto provide an oil which
  5. temperatureat reflux for 12 h
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customyielding a brown oil which
  8. customThe reaction mixture was purified in column chromatography (5% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-98b5b6c4ca6e4c908c7280faa5b61774
出典データセット
uspto-grants-2001_11
特許番号
US06316637B1

関連ノート

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