Dimethylformamide → N-Methyl-4-(4-nitrophenoxy)-2-nitroaniline

HRID 1294059ノート

反応式

HRID 1294059 の反応式
[H-].[Na+].[N+:3]([C:6]1[CH:22]=[CH:21][C:9]([O:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH3:23]N(C=O)C>>[CH3:23][NH:15][C:14]1[CH:16]=[CH:17][C:11]([O:10][C:9]2[CH:21]=[CH:22][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=2)=[CH:12][C:13]=1[N+:18]([O-:20])=[O:19]

参加物

4

反応物 3

HCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 12032722Benzenamine, 2-nitro-4-(4-nitrophenoxy)-2 回

生成物 1

HCID 17755333N-Methyl-4-(4-nitrophenoxy)-2-nitroaniline

反応条件

温度
0 °C

実験手順

To a mixture of NaH (60% oily, 320 mg, 8.0 mmol) in DMF (30 mL) was added a solution of 4-(4-nitrophenoxy)-2-nitroaniline (Intermediate 8A-2.00 g, 7.3 mmol) in DMF (30 mL) at 0° C. followed by an excess amount of Mel (2.0 mL). The mixture was stirred at 0° C. for 1.5 hrs then at room temperature overnight. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2column chromatography gave the title compound (2.10 g, quant). ): 1H NMR (CDCl3-d1) δ 3.08 (d, 3H), 6.94 (d, 1H), 7.00 (d, 2H), 7.30 (dd, 1H), 7.97 (d, 1H), 8.08 (brs, 1H), 8.22 (d, 2H).

後処理

  1. customat room temperature
  2. customovernight
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customthen evaporated
  7. customSequence purification on SiO2column chromatography

出典と根拠

ORDレコード
ord-9e94a474f9c74874bdfad9bf6adddf9a
出典データセット
uspto-grants-2007_07
特許番号
US07238813B2

反応ノート

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