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

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].[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

参加物

反応物 2

HCID 176Acetic Acid

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

生成物 1

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

実験手順

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).

後処理

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)

出典と根拠

ORDレコード: ord-9d893dcbf9fc41ed921e36f3dfd92431
出典データセット: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08778937B2

反応ノート

読み込み中…

参加物