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Sodium Hydroxide → 5-(2,6-Dimethyl-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfinylphenyl)-1,3-thiazole

HRID 1727363
Notes
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Reaction equation

HRID 1727363 reaction equation
[CH3:1][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]=[C:4]([CH3:28])[N:3]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.[OH-].[Na+]>CN(C)C=O>[CH3:28][C:4]1[CH:5]=[C:6]([C:8]2[S:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([CH3:20])=[O:37])=[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:7]=[C:2]([CH3:1])[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 102011465-(2,6-DIMETHYL-4-PYRIDYL)-4-(3-METHYLPHENYL)-2-[4-(METHYLTHIO)PHENYL]-1,3-THIAZOLE

Product 1

HCID 229326815-(2,6-Dimethyl-4-pyridyl)-4-(3-methylphenyl)-2-(4-methylsulfinylphenyl)-1,3-thiazoleYield 98%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 5-(2,6-dimethyl-4-pyridyl)-4-(3-methylphenyl)-2-[4-(methylthio)phenyl]-1,3-thiazole (0.41 g, 1.0 mmol) in N,N-dimethylformamide (15 mL) was added m-chloroperbenzoic acid (0.25 g, 1.0 mmol), and the mixture was stirred for 1 hour at room temperature. A 8N aqueous sodium hydroxide solution was poured into the reaction mixture, and extracted with ethyl acetate. The extracted solution was washed with brine, dried, then, the solvent was distilled off. The residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Lte.), hexane-ethyl acetate=1:2), to obtain a title compound (0.41 g, yield 97%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracted solution was washed with brine
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Lte.), hexane-ethyl acetate=1:2)

Sources & evidence

ORD record
ord-88302b6abd06480899ab3930ac1e9ff0
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495018B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes