Acetic Acid → 4-bromo-2-methyl-6-nitro-1H-benzo[d]imidazole

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].[C:13](O)(=O)[CH3:14]>>[Br:1][C:2]1[C:3]2[N:12]=[C:13]([CH3:14])[NH:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

참가 물질

반응물 2

HCID 176Acetic Acid

HCID 203480123-Bromo-5-nitrobenzene-1,2-diamine

생성물 1

HCID 866878134-bromo-2-methyl-6-nitro-1H-benzo[d]imidazole수율 56.6%

실험 절차

A mixture of 3-bromo-5-nitrobenzene-1,2-diamine (90 g, 389 mmol) in acetic acid (800 mL) was stirred under reflux for 18 h. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1) to give the product (56 g, 56.6%) as a brown solid; LC/MS: MS (ES+) m/e 256 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 2.60 (s, 3H), 8.20 (d, J=1.8 Hz, 3H), 8.34 (d, J=1.8 Hz, 2H), 13.25 (s, br, 1H).

후처리

temperatureunder reflux for 18 h
customThe solvent was removed in vacuo
customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1)

출처 및 근거

ORD 기록: ord-9d893dcbf9fc41ed921e36f3dfd92431
출처 데이터셋: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08778937B2

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