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

HRID 78308ノート

反応式

HRID 78308 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-64566831b3e948519452b0238460a809
出典データセット
uspto-grants-2014_09
特許番号
US08841330B2

反応ノート

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