Sodium Hydroxide → 5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazole

HRID 1178586Notes

Reaction equation

HRID 1178586 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:36])C=1.[OH-:39].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([CH3:20])(=[O:36])=[O:39])=[CH:17][CH:18]=3)=[N:10][C:9]=2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 101573605-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-[4-(methylthio)phenyl]-1,3-thiazole

Product 1

HCID 102739295-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazoleYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylthiophenyl)-1,3-thiazole (2.7 g, 6.9 mmol) in N,N-dimethylformamide (60 mL) was added m-chloroperbenzoic acid (3.3 g, 14 mmol) and the mixture was stirred at room temperature for 1 hour. An 8N aqueous solution of sodium hydroxide was added to the reaction mixture and the resulting solid was collected by filtration. This solid was recrystallized from ethanol to obtain 2.5 g (yield 85%) of the title compound.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. customThis solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-5c86f4166e5e4f2e99054a83ef585d04
Source dataset
uspto-grants-2007_10
Patent number
US07276527B2

Reaction notes

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