N-(4-bromo-2-nitrophenyl)acetamide → N-Acetyl 4-(3-furanyl)-2-nitroaniline

HRID 581950

반응식

HRID 581950 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2].[O:15]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16]1.C(=O)(O)[O-].[Na+]>O.C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:17]2[CH:18]=[CH:19][O:15][CH:16]=2)=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 136690N-(4-bromo-2-nitrophenyl)acetamideHCID 516892Sodium BicarbonateHCID 2734358Furan-3-boronic acid

생성물 1

HCID 54094756N-Acetyl 4-(3-furanyl)-2-nitroaniline수율 76%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

A mixture of 1d from Example 18 (8.5 g, 32.8 mmol), 3-furanylboronic acid (3.67 g, 32.8 mmol), sodium bicarbonate (13.8 g, 0.16 mol) and tetrakis(triphenylphosphine)palladium(0) (0.5 g) in a mixture of water (40 ml) and dimethoxyethane (80 ml) is heated to 80° C. under a stream of nitrogen over night. After cooling the mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with brine, dried over sodium sulfate and concentrated under reduced pressure.(*). The residue is dissolved in 40 ml dimethoxyethane. Aqueous sodium hydroxide (78 ml, 1 M) is added and the mixture is stirred at ambient temperature over night. The mixture is poured into water and rendered acidic with diluted hydrochloric acid. The precipitate is filtered off, washed with water and dried to yield 1e (5.09 g, 76%). Mp 152-154° C.

후처리

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue is dissolved in 40 ml dimethoxyethane
  7. additionAqueous sodium hydroxide (78 ml, 1 M) is added
  8. additionThe mixture is poured into water
  9. filtrationThe precipitate is filtered off
  10. washwashed with water
  11. customdried

출처 및 근거

ORD 기록
ord-3e5b9130d7dd4c5483cca17b90d6c1eb
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922724

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