Water → 6-bromo-2-isopropyl-4-nitro-1H-benzo[d]imidazole

HRID 44481

反応式

HRID 44481 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.O.C([O-])([O-])=O.[Na+].[Na+].[C:20](O)(=O)[CH:21]([CH3:23])[CH3:22]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]2[N:9]=[C:20]([CH:21]([CH3:23])[CH3:22])[NH:8][C:6]=2[CH:7]=1

参加物

5

反応物 4

HCID 962WaterHCID 6590Isobutyric AcidHCID 10340Sodium CarbonateHCID 457894035-Bromo-3-nitrobenzene-1,2-diamine

生成物 1

HCID 669767256-bromo-2-isopropyl-4-nitro-1H-benzo[d]imidazole収率 77%

反応条件

温度
120 °C

実験手順

A mixture of 5-bromo-3-nitrobenzene-1,2-diamine (prepared following the same procedure as for Example 1, 5.0 g) in isobutyric acid (20 mL) was stirred at 120° C. overnight. The mixture was cooled to room temperature and poured into water (100 mL). The pH was neutralized with aqueous Na2CO3 solution. It was then extracted with EtOAc and the organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered and concentrated in-vacuo. The residue was then purified by silica gel chromatography eluted with EtOAc:petroleum ether=1:1 to afford the desired product as a yellow solid (4.7 g, 77%). 1H NMR (300 MHz, CDCl3) δ ppm 1.51 (m, 6H, J=6.9 Hz), 3.32 (m, 1H, J=6.9 Hz), 8.16 (d, 1H, J=1.5 Hz), 8.25 (d, 1H, J=1.5 Hz), 10.26 (br s, 1H); LC-MS: m/e=284 [M+1]+

後処理

  1. customprepared
  2. temperatureThe mixture was cooled to room temperature
  3. extractionIt was then extracted with EtOAc
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in-vacuo
  8. customThe residue was then purified by silica gel chromatography
  9. washeluted with EtOAc

出典と根拠

ORDレコード
ord-ebce37c166bd418eac8733482eb3b24b
出典データセット
uspto-grants-2013_09
特許番号
US08541411B2

関連ノート

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