Triethylamine → HCID 87233421, Verbindung

HRID 1257993

Reaktionsgleichung

Reaktionsgleichung von HRID 1257993
[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:7]([CH3:25])=[C:8]([C:16]([C:18]3[CH:19]=[N:20][N:21]([CH3:24])[C:22]=3[OH:23])=[O:17])[CH:9]=[CH:10][C:11]=2[S:12]([CH3:15])(=[O:14])=[O:13])=[N:2]1.C(N(CC)CC)C.[CH3:33][CH2:34][S:35][C:36](Cl)=[O:37].C(OCC)(=O)C>O1CCCC1>[CH3:25][C:7]1[C:6]([C:3]2[CH2:4][CH2:5][O:1][N:2]=2)=[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=[CH:9][C:8]=1[C:16]([C:18]1[CH:19]=[N:20][N:21]([CH3:24])[C:22]=1[O:23][C:36]([S:35][CH2:34][CH3:33])=[O:37])=[O:17]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18056Ethyl chlorothioformateHCID 178428868HCID 178428868, Verbindung

Produkt 1

HCID 87233421HCID 87233421, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-hydroxy-1-methylpyrazol-4-yl 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)phenyl ketone (100 mg, 2.75×10−4 mol) in anhydrous tetrahydrofuran (5 mL) were added triethylamine (55 mg) and 96% S-ethyl chlorothiolformate (45 mg) at room temperature. After the reaction solution was stirred for 1 hour, 150 mL of ethyl acetate was added, and the solution was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4) to obtain the desired product (82 mg) as an oil.

Aufarbeitung

  1. washthe solution was washed twice with a saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4)

Quellen und Nachweise

ORD-Eintrag
ord-93c863f9e06e477fb60470aac27052b9
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466088B2

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