Ammonia → HCID 118033080, Verbindung

HRID 590524

Reaktionsgleichung

Reaktionsgleichung von HRID 590524
[CH3:1][N:2]1[C:6](=[O:7])[C:5]2([C:15]3[CH:14]=[CH:13][S:12][C:11]=3[CH2:10][CH2:9][CH2:8]2)[N:4]=[C:3]1SC.[I-].[NH4+:19].N>CO>[NH2:19][C:3]1[N:2]([CH3:1])[C:6](=[O:7])[C:5]2([C:15]3[CH:14]=[CH:13][S:12][C:11]=3[CH2:10][CH2:9][CH2:8]2)[N:4]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 25487Ammonium iodideHCID 1180330781'-Methyl-2'-(methylthio)-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one

Produkt 1

HCID 118033080HCID 118033080, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1′-Methyl-2′-(methylthio)-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one (1.5 g, 5.63 mmol), ammonium iodide (4.89 g, 33.78 mmol) and 7 N ammonia in methanol (20 mL) were heated at 90° C. for 12 h. The solvent was then evaporated under reduced pressure and the residue was partitioned between water and dichloromethane. The dichloromethane extracts were combined, dried over magnesium sulphate and evaporated under reduced pressure to give an oil. This consisted of the title compound as the major component and its minor regioisomer in a 2:1 ratio. The oil was loaded onto a Biotage SNAP cartridge and eluted with dichloromethane-dichloromethane/7N ammonia in methanol (9:1). The appropriate fractions were combined and evaporated under reduced pressure to give 2′-amino-1′-methyl-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one as a foam (800 mg, 60%).

Aufarbeitung

  1. customThe solvent was then evaporated under reduced pressure
  2. customthe residue was partitioned between water and dichloromethane
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-8272d6434bfd4a528cc703711973edfa
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233982B2

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