Methylamine → 4-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzene

HRID 898948노트

반응식

HRID 898948 반응식
[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(O)=[O:2].O=S(Cl)Cl.[CH3:26][NH2:27].[OH-].[Na+]>C(Cl)Cl>[CH3:26][NH:27][C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:2]

참가 물질

6

반응물 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 230230632-Methoxy-5-(4-nitrophenoxy)benzoic acid

생성물 1

HCID 206091394-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzene수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-(3-carboxy-4-methoxyphenoxy)-1-nitrobenzene (0.50 g, 1.75 mmol) in CH2Cl2 (12 mL) was added SOCl2 (0.64 mL, 8.77 mmol) in portions. The resulting solution was heated at the reflux temp. for 18 h, cooled to room temp., and concentrated under reduced pressure. The resulting yellow solids were dissolved in CH2Cl2 (3 mL) then the resulting solution was treated with a methylamine solution (2.0 M in THF, 3.5 mL, 7.02 mmol) in portions (CAUTION: gas evolution), and stirred at room temp. for 4 h. The resulting mixture was treated with a 1N NaOH solution, then extracted with CH2Cl2 (25 mL). The organic layer was dried (Na2SO4) and concentrated) under reduced pressure to give 4-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzene as a yellow solid (0.50 g, 95%).

후처리

  1. temperatureThe resulting solution was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting yellow solids were dissolved in CH2Cl2 (3 mL)
  5. extractionextracted with CH2Cl2 (25 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated) under reduced pressure

출처 및 근거

ORD 기록
ord-9c905e2a9a41401a82f108db32da6e45
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07351834B1

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