Pyridine → N-3-Quinolinylbenzenesulfonamide

HRID 394554노트

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HRID 394554 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N1C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.C(OCC)(=O)C>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([NH:1][S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[CH:3]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 113753-Aminoquinoline

생성물 1

HCID 16654646N-3-Quinolinylbenzenesulfonamide

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a solution of 3-aminoquinoline (7.2 g, 50 mmol) in acetonitrile (150 mL) was added pyridine (25 mL) and the resulting mixture was cooled to 0° C. A solution of benzenesulfonyl chloride (7 mL, 55 mmol) in acetonitrile (20 mL) was added dropwise over 30 minutes. The mixture was allowed to warm to rt and stirred for 18 hours. The mixture was diluted with ethyl acetate (100 mL) and washed successively with 1N HCl, brine and saturated CuSO4, dried (MgSO4), and concentrated in vacuo to afford an oil. Purification by flash silica gel column chromatography eluting with 30% ethyl acetate in hexanes afforded compound C (13. g g, 95%) as a white solid. MS; (M+H)+=285

후처리

  1. temperatureto warm to rt
  2. washwashed successively with 1N HCl, brine and saturated CuSO4
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford an oil
  6. customPurification by flash silica gel column chromatography
  7. washeluting with 30% ethyl acetate in hexanes afforded compound C (13. g g, 95%) as a white solid

출처 및 근거

ORD 기록
ord-be7dfc7e9e8c4e32b0ec01ae27d2bc73
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602883B1

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