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

HRID 1727363
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1727363
[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
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Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-88302b6abd06480899ab3930ac1e9ff0
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07495018B2

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