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

HRID 1771864노트

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HRID 1771864 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 59376804Methyl 4-(4-aminophenylthio)-3-nitrobenzoate수율 90%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 7914Diisopropyl Ether용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0d736717c6b949b4abecc32bd1afd42c
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249138B2

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