m-Chloroperbenzoic acid → HCID 16073909, compound

HRID 1068029Notes

Reaction equation

HRID 1068029 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][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]SC3C=CC(Cl)=CC=3)[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.O.[C:40]1(C)[CH:45]=[CH:44][C:43]([S:46]([OH:49])(=[O:48])=O)=[CH:42][CH:41]=1.[Cl:51]C1C=C(C=CC=1)C(OO)=O>ClCCl>[Cl:1][C:2]1[CH:38]=[CH:37][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:46]([C:43]3[CH:42]=[CH:41][C:40]([Cl:51])=[CH:45][CH:44]=3)(=[O:48])=[O:49])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 521998p-Toluenesulfonic acid monohydrateHCID 16073907N-[(4-chlorophenyl)methyl]-1-[(4-chlorophenyl)sulfanylmethyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

Product 1

HCID 16073909HCID 16073909, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(4-chlorobenzyl)-1-([(4-chlorophenyl)sulfanyl]methyl)-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.11 gm) from Example No. 101 in dichloromethane (2 mL) at 0° C. is treated with p-toluenesulfonic acid hydrate (0.04 gm) followed by m-chloroperoxybenzoic acid (˜85%) (0.09 gm). The mixture is stirred for 0.75 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 0.09 gm of the title compound as a white solid.

Workup

  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

Sources & evidence

ORD record
ord-77acd51ee4a64b8aa973482d5bbe86d3
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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