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

HRID 1294059노트

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HRID 1294059 반응식
[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]

참가 물질

4

반응물 3

HCID 6228Dimethylformamide2회HCID 24758Sodium hydrideHCID 12032722Benzenamine, 2-nitro-4-(4-nitrophenoxy)-2회

생성물 1

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

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9e94a474f9c74874bdfad9bf6adddf9a
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238813B2

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