Nitrogen → 2-fluoro-4-nitro-N-(3-(tetrahydrofuran-2-yl)propyl)aniline

HRID 56218ノート

反応式

HRID 56218 の反応式
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:19][CH2:20][CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1.N#N>CN(C=O)C>[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][CH2:19][CH2:20][CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1

参加物

6

反応物 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 1012542-Fluoro-4-nitroanilineHCID 146316702-(3-Chloropropyl)tetrahydrofuran

生成物 1

HCID 900235572-fluoro-4-nitro-N-(3-(tetrahydrofuran-2-yl)propyl)aniline収率 31%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

To a mixture of 2-fluoro-4-nitroaniline (7.02 g, 45.0 mmol), Cs2CO3 (29.3 g, 90.0 mmol), KI (16.6 g, 100 mmol) and DMF (100 mL) was added 2-(3-chloropropyl)tetrahydrofuran (7.43 g, 50.0 mmol) dropwise under N2 and the mixture was stirred at 140° C. for 48 h. The mixture was cooled to rt and filtered and the filtrate was concentrated in vacuo. To the residue was added water (30 mL) and the mixture was extracted with DCM (30 mL×4). The combined organic layers were washed with brine (40 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=20:1) to give the title compound as a yellow solid (3.74 g, 31%).

後処理

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo the residue was added water (30 mL)
  5. extractionthe mixture was extracted with DCM (30 mL×4)
  6. washThe combined organic layers were washed with brine (40 mL×2)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=20:1)

出典と根拠

ORDレコード
ord-4d5e48ab23424f4492284be4d5fa2e21
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

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