Water → tert-Butyl (5-formylpyrazin-2-yl)carbamate

HRID 385609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385609
Br[CH2:2][C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1.O.O.C[N+]([O-:23])(C)C.O.C(Cl)(Cl)Cl>CS(C)=O.ClCCl>[CH:2]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1)=[O:23]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6212ChloroformHCID 198430Trimethylamine oxide dihydrateHCID 45073740tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

Produkt 1

HCID 44118835tert-Butyl (5-formylpyrazin-2-yl)carbamateAusbeute 75,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixed solution of 0.17 g of tert-butyl (5-(bromomethyl)pyrazin-2-yl)carbamate in 4 mL of dimethyl sulfoxide and 2 mL of dichloromethane, 0.26 g of trimethylamine N-oxide dihydrate was added under cooling with ice, and the mixture was stirred for 2 hours. Thereto were added water and chloroform, the organic layer was separated, and washed with a saturated aqueous sodium hydrogen carbonate solution, water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.10 g of tert-butyl (5-formylpyrazin-2-yl)carbamate as a white solid.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. customthe organic layer was separated
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution, water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-db6e074454a145b28dd28dcb5a3fcc26
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367831B2

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