Formic Acid → 7-Bromo-5-nitro-1H-benzimidazole

HRID 1622459ノート

反応式

HRID 1622459 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([NH2:11])[C:3]=1[NH2:12].[CH:13](O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]2[N:12]=[CH:13][NH:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

参加物

4

反応物 2

HCID 284Formic AcidHCID 203480123-Bromo-5-nitrobenzene-1,2-diamine

生成物 1

HCID 532566897-Bromo-5-nitro-1H-benzimidazole収率 96.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a 100 mL round bottomed flask was added 3-bromo-5-nitrobenzene-1,2-diamine (5 g, 21.55 mmol) and formic acid (3.25 mL, 86 mmol) in Toluene (10 mL). The solution was heated to reflux overnight. The product precipitated and was triturated with toluene, diluted with water and adjusted to ph 9 with 6N NaOH. The solid was filtered, washed with water and placed in a vacuum oven overnight to yield 4-bromo-6-nitro-1H-benzo[d]imidazole (5.02 g, 20.74 mmol, 96% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.16 (s, 1H) 8.29 (d, J=2.02 Hz, 1H) 8.51 (d, J=2.02 Hz, 1H) 8.66 (s, 1H); LC/MS: MS (ES+) m/e 243 [M+H]+.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. customThe product precipitated
  4. customwas triturated with toluene
  5. additiondiluted with water and adjusted to ph 9 with 6N NaOH
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customplaced in a vacuum oven overnight

出典と根拠

ORDレコード
ord-d940db27c1db4e6cbcb8c0bfcece20e1
出典データセット
uspto-grants-2014_07
特許番号
US08778937B2

反応ノート

読み込み中…