Ammonium Chloride → 4-(pentylamino)-1H-imidazole-5-carbothioamide

HRID 249790

Reaktionsgleichung

Reaktionsgleichung von HRID 249790
[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH3:5].O.O.[SH2:16].[Na].[Cl-].[NH4+]>CO>[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12](=[S:16])[NH2:13])[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 451205654-(pentylamino)-1H-imidazole-5-carbonitrileHCID 86584117Sodium hydrogen sulfide dihydrate

Produkt 1

HCID 598538144-(pentylamino)-1H-imidazole-5-carbothioamideAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(pentylamino)-1H-imidazole-5-carbonitrile (25 g, 0.14 mol), sodium hydrogen sulfide dihydrate (26 g, 0.28 mol) and ammonium chloride (7.5 g, 0.14 mol) in methanol (400 mL) was stirred at room temperature overnight. The conversion was about 60% according to analytical LCMS. The mixture was then stirred at 50° C. for 3 hours. The methanol was removed and the residue was diluted with water and EtOAc. The organic layer was washed with water and brine respectively, dried and concentrated to yield the crude product (30.0 g), which was used for next step without further purification. LCMS calculated for C9H17N4S (M+H): 213.1. found: 213.1.

Aufarbeitung

  1. stirringThe mixture was then stirred at 50° C. for 3 hours
  2. customThe methanol was removed
  3. additionthe residue was diluted with water and EtOAc
  4. washThe organic layer was washed with water and brine respectively
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6a98747a9b36497e98c4e4f0e9fb1e80
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863285B2

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