4-Toluenesulfonyl chloride → HCID 118324003, compound

HRID 1778286Notes

Reaction equation

HRID 1778286 reaction equation
C1(C)C=CC(S(Cl)(=O)=[O:8])=CC=1.[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH:23]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:24]3[S:25][CH:26]=[CH:27][N:28]=3)[CH:21]=2)[N+:16]([O-])=[CH:15][CH:14]=1>ClCCl.C([O-])([O-])=O.[Na+].[Na+].O>[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH:23]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:24]3[S:25][CH:26]=[CH:27][N:28]=3)[CH:21]=2)[NH:16][C:15](=[O:8])[CH:14]=1

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1183240154-Bromo-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinoline 1-oxide

Product 1

HCID 118324003HCID 118324003, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

p-Toluenesulfonyl chloride (628 mg, 3.293 mmol, 1.5 equip) was added to a biphasic mixture of 4-bromo-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinoline 1-oxide in dichloromethane (6 mL) and 10% Na2CO3 (42 mL) and the resulting mixture stirred for 1 h. The reaction mixture was diluted with dichloromethane and water, the layers were separated, and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The residue was purified by MPLC to yield 4-bromo-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinolin-2(1H)-one as a white solid.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by MPLC

Sources & evidence

ORD record
ord-3d2599b416094221b30a7971c4db2e80
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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