Chlorosuccinimide → Ethyl 4-chloro-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate

HRID 554219노트

반응식

HRID 554219 반응식
[CH3:1][C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:18]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:18][C:5]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[NH:3][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 12258777Ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate

생성물 1

HCID 12808304Ethyl 4-chloro-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate수율 44.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution (20 mL) of ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate (1.0 g) in N,N-dimethylformamide was added N-chlorosuccinimide (874 mg) at 0° C. The reaction mixture was stirred at room temperature for 4 hr, 6% aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as colorless crystals (yield 509 mg, 44%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

출처 및 근거

ORD 기록
ord-8ae35762928e4c3dbc0d5c2cdd80c8af
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048909B2

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