Water → Methyl 4-(4-aminophenylthio)-3-nitrobenzoate

HRID 605330ノート

反応式

HRID 605330 の反応式
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([S:22][C:19]2[CH:20]=[CH:21][C:16]([NH2:15])=[CH:17][CH:18]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145104-AminothiophenolHCID 735797Methyl 4-chloro-3-nitrobenzoate

生成物 1

HCID 59376804Methyl 4-(4-aminophenylthio)-3-nitrobenzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-chloro-3-nitrobenzoic acid methyl ester (15.0 g, 68 mmol), 4-aminothiophenol (8.8 g, 68 mmol) and K2CO3 (11.8 g, 85 mmol) in DMF (150 mL) was heated at 90° C. for 1.5 hours, cooled to room temperature, and then poured into H2O (450 mL) under stirring. The aqueous mixture was extracted with AcOEt (400 mL). The extract was washed with H2O (3 times) and brine, dried over MgSO4, and evaporated to give the crude product as orange crystal. The crude product was suspended in 150 mL of i-Pr2O and stirred at room temperature for 1 hour. The crystal was collected by filtration, washed with i-Pr2O and dried at 60° C. for 3 days under reduced pressure to give purified title compound as orange crystal (18.6 g, 90%).

後処理

  1. temperaturecooled to room temperature
  2. extractionThe aqueous mixture was extracted with AcOEt (400 mL)
  3. washThe extract was washed with H2O (3 times) and brine
  4. dry with materialdried over MgSO4
  5. customevaporated

出典と根拠

ORDレコード
ord-db209f52fade422e9754b498ad3640ad
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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