2-Nitro-1H-benzimidazole → 2-Isopropyl-1H-benzo[d]imidazol-5-amine

HRID 2304728

反応式

HRID 2304728 の反応式
[N+](C1C=CC(N)=C(N)C=1)([O-])=O.[CH:12]([C:15]1[NH:16][C:17]2[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:18]=2[N:19]=1)([CH3:14])[CH3:13].[N+](C1NC2C=CC=CC=2N=1)([O-])=O>C(O)(=O)C(C)C.CCOC(C)=O.CO.[Pd]>[CH:12]([C:15]1[NH:16][C:17]2[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:18]=2[N:19]=1)([CH3:14])[CH3:13]

参加物

8

反応物 3

HCID 972342-Nitro-1H-benzimidazoleHCID 6832022-Isopropyl-5-nitro-1H-benzo[d]imidazoleHCID 51117914-Nitro-1,2-phenylenediamine

生成物 1

HCID 8207492-Isopropyl-1H-benzo[d]imidazol-5-amine収率 92%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6590Isobutyric Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-nitro-1,2-phenylenediamine (0.9 g, 5.9 mmol) in 5 ml of isobutyric acid was stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo to yield a dark brown residue, which was dissolved in 100 ml of EtOAc and washed with aqueous NaHCO3. Organic layer was dried over MgSO4 and concentrated in vacuo, yielding an oil which was characterized as 2-isopropyl-5-nitrobenzimidazole and subjected to a following reaction without further purification. The nitrobenzimidazole and 50 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 0.95 g (5.4 mmol, 92%) 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 dark brown residue, which
  4. washwashed with aqueous NaHCO3
  5. dry with materialOrganic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customyielding an oil which
  8. customsubjected to a 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-b3d879143f594bd0a0678c7228c87034
出典データセット
uspto-grants-2002_08
特許番号
US06436982B1

関連ノート

読み込み中…