Dimethyl Sulfate → 3-(2-Nitro-2-methylpropyl)-7-nitroindole

HRID 8129

Reaktionsgleichung

Reaktionsgleichung von HRID 8129
CN([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([N+:14]([O-:16])=[O:15])[C:8]=2[NH:7][CH:6]=1)C.COS(OC)(=O)=O.C[O-].[Na+]>[N+](C(C)C)([O-])=O.CO>[N+:14]([C:13]([CH3:8])([CH3:12])[CH2:4][C:5]1[C:9]2[C:8](=[C:13]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:11][CH:10]=2)[NH:7][CH:6]=1)([O-:16])=[O:15]

Komponenten

6

Edukt 3

HCID 6497Dimethyl SulfateHCID 15451Indole, 3-((dimethylamino)methyl)-7-nitro-HCID 10942334Sodium Methoxide

Produkt 1

HCID 220147673-(2-Nitro-2-methylpropyl)-7-nitroindoleAusbeute 131 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3982-NitropropaneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

The 7-nitrogramine salt (2.0 g, 5.8 mmol) is suspended in a mixture of 2-nitropropane (9.5 mL) and methanol (9.5 mL). Dimethylsulfate (1.09 mL, 11.5 mmol) is added dropwise via syringe, and the resulting yellow solution is stirred at room temperature for 5 minutes. Sodium methoxide (0.62 g, 11.5 mmol) is then added in one portion, and the mixture is stirred overnight at room temperature. The reaction is quenched by addition of saturated NH4Cl solution and ethyl acetate. The aqueous layer is extracted with ethyl acetate, and the combined organic layers are washed with brine, and dried over Na2SO4 to give 1.0 g of 3-(2-nitro-2-methylpropyl)-7-nitroindole (69%).

Aufarbeitung

  1. stirringthe mixture is stirred overnight at room temperature
  2. customThe reaction is quenched by addition of saturated NH4Cl solution and ethyl acetate
  3. extractionThe aqueous layer is extracted with ethyl acetate
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-8866daba5bfc47cba6e2aaa9a9e6d8c6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087635B2

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