m-Chloroperbenzoic acid → 1-(benzenesulfinylmethyl)-N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068014노트

반응식

HRID 1068014 반응식
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH2:28][S:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=[O:46])=CC=1.ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH2:28][S:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:46])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 521998p-Toluenesulfonic acid monohydrateHCID 9915062N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-1-(phenylsulfanylmethyl)quinoline-3-carboxamide

생성물 1

HCID 160738921-(benzenesulfinylmethyl)-N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide수율 72.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of N-(4-chlorobenzyl)-6-(4-morpholinylmethyl)-4-oxo-1-[(phenylsulfanyl)methyl)-1,4-dihydro-3-quinolinecarboxamide (0.08 gm) from Example No. 76 in dichloromethane (2 mL) at 0° C. is added p-toluenesulfonic acid hydrate (0.03 gm) followed by m-chloroperoxybenzoic acid (˜85%) (0.03 gm). The mixture is stirred for 1 hr. The reaction mixture is diluted with dichloromethane, washed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by recrystallization from acetonitrile to afford 0.06 gm of the title compound as a white solid.

후처리

  1. washwashed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified by recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-dc4097f6f1c14d6494d639a146d93c03
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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