3-Nitrophenol → N-cyclopropyl-2-(3-nitrophenoxy)acetamide

HRID 1487106

반응식

HRID 1487106 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[CH:16]1([NH:15][C:13](=[O:14])[CH2:12][O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:18][CH2:17]1

참가 물질

6

반응물 3

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 7357802-chloro-N-cyclopropylacetamide

생성물 1

HCID 7865440N-cyclopropyl-2-(3-nitrophenoxy)acetamide수율 61.9%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A mixture of 3-nitrophenol (4 g, 28.8 mmol), 2-chloro-N-cyclopropylacetamide (4.61 g, 34.5 mmol), K2CO3 (7.95 g, 57.5 mmol) and 18-CROWN-6 (0.228 g, 0.863 mmol) in N,N-Dimethylformamide (30.0 ml) was stirred under N2 atmosphere for 18 hrs at 50° C. After cooling to RT, the reaction mixture was partitioned between EtOAc (250 ml) and water (250 ml). Aq. phase was re-extracted with EtOAc (200 ml). Combined organic layer was washed with brine (100 ml), dried over sodium sulphate and the solvent was evaporated under vacuum. Crude residue was purified by flash chromatography to obtain N-cyclopropyl-2-(3-nitrophenoxy)acetamide (4.21 gm).

후처리

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was partitioned between EtOAc (250 ml) and water (250 ml)
  3. extractionAq. phase was re-extracted with EtOAc (200 ml)
  4. washCombined organic layer was washed with brine (100 ml)
  5. dry with materialdried over sodium sulphate
  6. customthe solvent was evaporated under vacuum
  7. customCrude residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-2cf8359757694e178b0fe0770e9370cb
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428499B2

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