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

HRID 1068014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068014
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 160738921-(benzenesulfinylmethyl)-N-[(4-chlorophenyl)methyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamideAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dc4097f6f1c14d6494d639a146d93c03
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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