Sodium Azide → 4-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

HRID 275424

Reaktionsgleichung

Reaktionsgleichung von HRID 275424
Br[CH:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3]1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O>[N:16]([CH:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3]1)=[N+:17]=[N-:18]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 102446284-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Produkt 1

HCID 101051694-azido-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyranAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (6.73 g, 25.29 mmoles), title B compound, in dry N,N-dimethylformamide (100 mL) was treated with sodium azide (3.79 g, 50.57 mmoles) and stirred at room temperature under argon for 4 hours. The reaction mixture was partitioned between 100 mL ethyl acetate and 200 mL distilled water. The organic layer was separated and the aqueous layer was extracted with 100 mL of ethyl acetate. The combined organics were washed successively with distilled water, saturated sodium bicarbonate solution, brine and dried over magnesium sulfate. The solvent was evaporated under vacuum to obtain an orange gum (5.62 g) which was triturated with pentane to provide the title compound (4.50 g, 78%) as an off-white solid, m.p. 63°-64° C. Microanalysis calculated for C12H12N4O: C, 63.15; H, 5.30; N, 24.55. Found: C, 63.57; H, 5.27; N, 24.75.

Aufarbeitung

  1. customThe reaction mixture was partitioned between 100 mL ethyl acetate and 200 mL
  2. distillationdistilled water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 100 mL of ethyl acetate
  5. washThe combined organics were washed successively with distilled water, saturated sodium bicarbonate solution, brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4fb4a803029948daa40f4c088aa414c8
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393771

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