Pyridine → S-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamothioate

HRID 1258608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258608
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1.N1C=CC=CC=1.[C:30](=[O:37])(Cl)[S:31][CH2:32][CH2:33][CH2:34][CH3:35]>ClCCl>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH:23][C:30](=[O:37])[S:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:5][N:4]=[N:3]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 13295035S-Butyl carbonochloridothioateHCID 768322206-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

Produkt 1

HCID 86653155S-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamothioateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine (150.0 mg, 0.485 mmol) in dichloromethane (5 mL), under argon atmosphere, were added pyridine (0.078 mL, 0.97 mmol) and S-butyl carbonochloridothioate (133 mg, 0.87 mmol) at room temperature. After stirring at room temperature overnight, the reaction mixture was diluted with dichloromethane (50 mL), filtered through “Chem Elut” cartridge, washed with dichloromethane (50 mL) and the filtrate was concentrated in vacuo yielding to S-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamothioate as a honey [82 mg, yield 38%; HPLC/MS m/z=426 (M+H); logP(HCOOH)=4.25].

Aufarbeitung

  1. filtrationfiltered through “Chem Elut” cartridge
  2. washwashed with dichloromethane (50 mL)
  3. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d533addda7294dd3967c6f5b2d46bd04
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466176B2

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