Hydroxyamine hydrochloride → N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

HRID 1258590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258590
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)=O)[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:18][OH:19]>N1C=CC=CC=1>[OH:19][N:18]=[C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([S:2][CH3:1])[CH:4]=1)[C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 67189850[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone

Produkt 1

HCID 136352704N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimineAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirred solution of [3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone (5.62 g, 24 mmol) in dry pyridine (30 mL) was added hydroxylamine hydrochloride (4.17 g, 60 mmol). The reaction mixture was stirred at 70° C. for 5 h, then concentrated in vacuo and diluted with ethyl acetate (100 mL) and water (50 mL). The organic layer was separated, washed with water (50 mL) and dried over MgSO4. Evaporation of the solvent in vacuo afforded N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine as a yellow solid [6.91 g, yield 99.3%; HPLC/MS: m/z=250 (M+H); logP(HCOOH)=1.98].

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate (100 mL) and water (50 mL)
  3. customThe organic layer was separated
  4. washwashed with water (50 mL)
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5dd3c9ee06fe42ccb4dcbff9a3aa420d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466176B2

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