4-Chloro-3-nitrotoluene → N-[3-Fluoro-4-(4-methyl-2-nitro-phenylsulfanyl)-phenyl]-acetamide

HRID 2358581ノート

反応式

HRID 2358581 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].ClC1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]

参加物

5

反応物 2

HCID 69764-Chloro-3-nitrotolueneHCID 68459196N-(3-Fluoro-4-methylsulfanyl-phenyl)-acetamide

生成物 1

HCID 68460909N-[3-Fluoro-4-(4-methyl-2-nitro-phenylsulfanyl)-phenyl]-acetamide収率 65%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

The product from Example 39c (1.00 g, 5.0 mmol) and t-BuSNa (1.88 g, 15.1 mmol) in anhydrous DMF (10 mL) was heated at 160° C. for 4 hours under N2 flow, and then cooled to room temperature. To the reaction mixture was added 1-chloro-4-methyl-2-nitrobenzene (2.36 mL, 17.6 mmol) at room temperature and then the mixture was heated at 80° C. for 4 hours under N2 flow. The mixture was diluted with H2O and then extracted with EtOAc. The extract washed with H2O and brine, dried over MgSO4, and evaporated. The residue was purified by silica gel column chromatography eluting with 2:1 EtOAc/hexane to give the title compound as yellow crystals (1.04 g, 65%).

後処理

  1. temperaturethe mixture was heated at 80° C. for 4 hours under N2 flow
  2. extractionextracted with EtOAc
  3. washThe extract washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 2:1 EtOAc/hexane

出典と根拠

ORDレコード
ord-b236311b837e499780595771d5a450b6
出典データセット
uspto-grants-2010_07
特許番号
US07763731B2

反応ノート

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