Dimethylformamide → 4-(Pyrrolidin-1-yl)benzene-1-sulfonyl chloride

HRID 641911

반응식

HRID 641911 반응식
CN(C=O)C.[N:6]1([C:11]2[CH:16]=[CH:15][C:14]([S:17]([OH:20])(=O)=[O:18])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.C(Cl)(=O)C([Cl:24])=O>ClCCl>[N:6]1([C:11]2[CH:16]=[CH:15][C:14]([S:17]([Cl:24])(=[O:20])=[O:18])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 221471014-(Pyrrolidin-1-YL)benzenesulfonic acid

생성물 1

HCID 534150104-(Pyrrolidin-1-yl)benzene-1-sulfonyl chloride수율 19%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

DMF (0.5 mL) was added to solution of 4-(pyrrolidin-1-yl)benzenesulfonic acid (7.3 g, 32.16 mmol) in dichloromethane (40 mL). Oxalyl chloride (10 g, 78.74 mmol) was then dropwise and the resulting solution was maintained at room temperature for 1 hour. The reaction mixture was then quenched by the addition of 40 mL of iced water. The resulting solution was extracted using dichloromethane (3×20 mL), and the organic layers were combined, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to afford 1.5 g (19%) of 4-(pyrrolidin-1-yl)benzene-1-sulfonyl chloride as a yellow solid. 1H NMR (CDCl3) δ 7.78 (d, 2H), 6.55 (d, 2H), 3.41 (t, 4H), 2.03 (t, 4H).

후처리

  1. customThe reaction mixture was then quenched by the addition of 40 mL of iced water
  2. extractionThe resulting solution was extracted
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-3aba208444d5408d908318debc6221c1
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696229B2

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