Dimethyl Sulfate → 3-fluoro-N-methyl-5-nitrobenzamide

HRID 522913ノート

反応式

HRID 522913 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([NH2:7])=[O:6].[C:14](=O)([O-])[O-].[Cs+].[Cs+].S(OC)(OC)(=O)=O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([NH:7][CH3:14])=[O:6]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 509984493-Fluoro-5-nitrobenzamide

生成物 1

HCID 594427293-fluoro-N-methyl-5-nitrobenzamide収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-fluoro-5-nitrobenzamide (1.0 g, 5.43 mmoL) in DMF (17 mL) was added cesium carbonate (2.6 g, 8.14 mmoL) and dimethyl sulphate (547 mg, 4.34 mmol) and the reaction mixture was stirred at RT for 24 h. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×40 ml). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-fluoro-N-methyl-5-nitrobenzamide (0.800 g, 80%) as a solid. Observed mass (M−1): 196.9.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (2×40 ml)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel column chromatography

出典と根拠

ORDレコード
ord-9c024b6c0bdc419e8090b4c52da45f4b
出典データセット
uspto-grants-2016_05
特許番号
US09334269B2

反応ノート

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