Triethylamine → (3-Fluoro-4-nitro-phenyl)-pyrrolidin-1-yl-methanone

HRID 18606

反応式

HRID 18606 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH2:18]([N:20](CC)[CH2:21][CH3:22])[CH3:19].N1CCCC1>C1C=CC=CC=1.CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:5]([N:20]2[CH2:21][CH2:22][CH2:19][CH2:18]2)=[O:7])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 2306533-Fluoro-4-nitrobenzoic acid

生成物 1

HCID 55103417(3-Fluoro-4-nitro-phenyl)-pyrrolidin-1-yl-methanone

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

1.00 g (5.40 mmol) 3-Fluoro-4-nitro-benzoic acid were suspended in 55 mL benzene. 1 mL Thionyl chloride and 7 drops DMF were added. The resulting mixture was stirred of 5 h at 70° C. and then concentrated under reduced pressure. The residue was dissolved in 40 mL CH2Cl2. Subsequently 0.75 mL (5.40 mmol) triethylamine and 0.45 mL (5.40 mmol) pyrrolidine were added and the resulting solution was stirred for 1 h at room temperature. The mixture was diluted with CH2Cl2 and washed subsequently with a 0.1 N HCl-solution, with a saturated NaHCO3-solution and with brine. The organic layer was dried over anhydrous MgSO4 and concentrated under vacuo to give crude (3-Fluoro-4-nitro-phenyl)-pyrrolidin-1-yl-methanone as an orange solid.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 40 mL CH2Cl2
  3. stirringthe resulting solution was stirred for 1 h at room temperature
  4. washwashed subsequently with a 0.1 N HCl-solution, with a saturated NaHCO3-solution and with brine
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated under vacuo

出典と根拠

ORDレコード
ord-5f9779b5c3244eb2a6fd38a7490201d2
出典データセット
uspto-grants-2010_06
特許番号
US07741341B2

関連ノート

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