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

HRID 1622459노트

반응식

HRID 1622459 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 532566897-Bromo-5-nitro-1H-benzimidazole수율 96.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-d940db27c1db4e6cbcb8c0bfcece20e1
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778937B2

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