Methylamine → Nizax

HRID 1108851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108851
[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].[C:10](#[N:12])C.CN.Cl.Cl.Cl[CH2:18][C:19]1[N:20]=[C:21]([CH2:24][N:25]([CH3:27])[CH3:26])[S:22][CH:23]=1>O>[CH3:10][NH:12]/[C:5](/[NH:9][CH2:8][CH2:7][S:6][CH2:18][C:19]1[N:20]=[C:21]([CH2:24][N:25]([CH3:27])[CH3:26])[S:22][CH:23]=1)=[CH:4]\[N+:1]([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 6329MethylamineHCID 6342AcetonitrileHCID 38355832-Nitromethylene-thiazolidineHCID 187843234-Chloromethyl-2-dimethylaminomethylthiazole dihydrochloride

Produkt 1

HCID 3033637NizaxAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 2-nitromethylenethiazolidine (11.95 g) and acetonitrile (154 ml) was stirred and heated at 40° C. and then methylamine (31.7 ml of a 40% w/w aqueous solution) was added in one batch. A solution of 4-chloromethyl-2-dimethylaminomethylthiazole dihydrochloride (21.5 g) in water (21.5 ml) was added dropwise to the reaction mixture over 50 minutes. The mixture was then stirred for 2.5 hours and then the solvent was removed under reduced pressure to give an oil. The oil was dissolved in water (150 ml) and extracted with dichloromethane (3×150 ml). The combined extracts were dried and evaporated to give nizatidine (19.2 g, 70.6% yield). The crude material was 86.8% pure by HPLC.

Aufarbeitung

  1. stirringThe mixture was then stirred for 2.5 hours
  2. customthe solvent was removed under reduced pressure
  3. customto give an oil
  4. extractionextracted with dichloromethane (3×150 ml)
  5. customThe combined extracts were dried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2d007d6b43fe4a858da67ab897f3adde
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06069256

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