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

HRID 1771864ノート

反応式

HRID 1771864 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.O(C(C)C)C(C)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

7

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収率 90%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 7914Diisopropyl Ether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 ethyl acetate (400 mL). The extract was washed with H2O (3 times) and brine, dried over MgSO4, and evaporated to give the crude produce 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 gave purified title compound as orange crystal (18.6 g, 90% yield).

後処理

  1. temperaturecooled to room temperature
  2. extractionThe aqueous mixture was extracted with ethyl acetate (400 mL)
  3. washThe extract was washed with H2O (3 times) and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give the crude
  7. customproduce as orange crystal
  8. stirringstirred at room temperature for 1 hour
  9. filtrationThe crystal was collected by filtration
  10. washwashed with i-Pr2O
  11. customdried at 60° C. for 3 days under reduced pressure
  12. customgave

出典と根拠

ORDレコード
ord-0d736717c6b949b4abecc32bd1afd42c
出典データセット
uspto-grants-2016_02
特許番号
US09249138B2

反応ノート

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