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Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → Methyl (1-methyl-5-(4-aminophenoxy)-benzimidazol-2-yl)carbamate

HRID 1294060
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1294060
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[CH:5][C:4]=1[N+:19]([O-])=O.[CH3:22][O:23][C:24]([NH:26][C:27](=NC(OC)=O)SC)=[O:25]>CO.[Pd]>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][C:6]([O:9][C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=3)=[CH:5][C:4]=2[N:19]=[C:27]1[NH:26][C:24](=[O:25])[O:23][CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 17755333N-Methyl-4-(4-nitrophenoxy)-2-nitroaniline2×

Produkt 1

HCID 17755417Methyl (1-methyl-5-(4-aminophenoxy)-benzimidazol-2-yl)carbamateAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

To a mixture of N-methyl-4-(4-nitrophenoxy)-2-nitroaniline (Intermediate 8B -2.10 g, 2.27 mmol) in MeOH (100 mL) was added 5% Pd—C (catalytic amount) and stirred at room temperature under H2 atmosphere. After 7 hrs, the catalyst was removed by filtration then the solvent was evaporated off. The residual mixture was dissolved into MeOH (50 mL) and added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (3.0 g, 14.5 mmol). The mixture was refluxed overnight. The solvent was removed by evaporation and sequence purification on SiO2 column chromatography gave title compound (87.3 mg, 4%): MS m/e 313 (M+1).

Aufarbeitung

  1. customthe catalyst was removed by filtration
  2. customthe solvent was evaporated off
  3. dissolutionThe residual mixture was dissolved into MeOH (50 mL)
  4. temperatureThe mixture was refluxed overnight
  5. customThe solvent was removed by evaporation and sequence purification on SiO2 column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a226441c0c6e4a14bc2bb4b2c4e62e57
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07238813B2

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