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

HRID 1068014ノート

反応式

HRID 1068014 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dc4097f6f1c14d6494d639a146d93c03
出典データセット
uspto-grants-2001_06
特許番号
US06248739B1

反応ノート

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