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

HRID 1487106ノート

反応式

HRID 1487106 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2855718-Crown-6触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2cf8359757694e178b0fe0770e9370cb
出典データセット
uspto-grants-2016_08
特許番号
US09428499B2

反応ノート

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