2,5-Dimethylphenyl isothiocyanate → 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarbothioamide

HRID 1802319

Reaktionsgleichung

Reaktionsgleichung von HRID 1802319
[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1[N:31]=[C:32]=[S:33]>ClCCl>[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:32](=[S:33])[NH:31][C:25]5[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]=5[CH3:23])[CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 1404992,5-Dimethylphenyl isothiocyanateHCID 666184764-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidine2×

Produkt 1

HCID 866476744-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-N-(2,5-dimethylphenyl)-1-piperidinecarbothioamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidine (i.e. the product of Step B) (1.0 g, 3.2 mmol) in dichloromethane (10 mL) was added a solution of 2,5-dimethylphenyl isothiocyanate (0.52 g, 3.2 mmol) and dichloromethane (5 mL) over 1 minute. The reaction mixture was stirred at room temperature for 20 minutes, concentrated, dissolved in methyl acetate (4 mL), held at 0° C. overnight and filtered to give the title compound as a white powder (1.35 g) melting at 120-123° C.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutiondissolved in methyl acetate (4 mL)
  3. waitheld at 0° C. overnight
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-acbf7d63d6f0415ba58c187817ed7239
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349870B2

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