Sodium hydride → Methyl 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carboxylate

HRID 398795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 398795
[H-].[Na+].[NH2:3][C:4]1[S:5][C:6]([CH3:13])=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22]>O1CCCC1>[N+:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:3][C:4]1[S:5][C:6]([CH3:13])=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10])([O-:23])=[O:22]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 675878Methyl-2-amino-5-methyl-3-thiophenecarboxylate

Produkt 1

HCID 19592005Methyl 5-methyl-2-((2-nitrophenyl)amino)thiophene-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred suspension of sodium hydride (2 g) in dry tetrahydrofuran (25 mL) under a nitrogen atmosphere was added a solution of methyl 2-amino-5-methylthiophene-3-carboxy-late (4.8 g, 0.028 mol) and 2-fluoronitrobenzene (4.0 g, 0.025 mol) in dry tetrahydrofuran (30 mL). The mixture was stirred at 25° C. for 20 hours, poured onto ice and partitioned between 2N hydrochloric acid and ethyl acetate. The organic extracts were dried over magnesium sulfate, the solvent was evaporated under reduced pressure and the title compound purified by chromatography on silica gel, eluted with toluene, and crystallized from ethanol (4.1 g).

Aufarbeitung

  1. additionpoured onto ice
  2. custompartitioned between 2N hydrochloric acid and ethyl acetate
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe title compound purified by chromatography on silica gel
  6. washeluted with toluene
  7. customcrystallized from ethanol (4.1 g)

Quellen und Nachweise

ORD-Eintrag
ord-df4679a3d287420599e46f87f3d1c331
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817657

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