Benzyl isocyanate → 4-(3-Benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide
Reaktionsgleichung
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([CH3:20])=[C:17]([NH2:19])[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH2:21]([N:28]=[C:29]=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([CH3:20])=[C:17]([NH:19][C:29]([NH:28][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:30])[CH:18]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 5-methyl-4-amino-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide from Step 2 (0.6 g, 2.1 mmol) and benzyl isocyanate (0.28 g, 2.1 mmol) in 1,4-dioxane (100 mL) was stirred under an inert atmosphere and heated to reflux. After 30 minutes, the mixture was allowed to cool, and the solvent was removed under reduced pressure. The residue was triturated in a small amount of acetonitrile, cooled, and filtered to afford 0.33 g of 4-(3-benzyl-ureido)-5-methyl-thiophene-2-carboxylic acid (1,3-benzodioxol-5-ylmethyl)-amide. A sample was recrystallized from methanol to give product with a mp 194-195° C.
Aufarbeitung
- temperatureheated to reflux
- temperatureto cool
- customthe solvent was removed under reduced pressure
- customThe residue was triturated in a small amount of acetonitrile
- temperaturecooled
- filtrationfiltered
Quellen und Nachweise
- ORD-Eintrag
- ord-b6767c996fff46b09cdeac2da97f0e15
- Quelldatensatz
- uspto-grants-2005_08
- Patentnummer
- US06924276B2
Notizen zur Reaktion
Wird geladen…