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

HRID 18606

반응식

HRID 18606 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 241Benzene용매HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f9779b5c3244eb2a6fd38a7490201d2
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741341B2

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