Sodium Azide → HCID 19361720, Verbindung

HRID 376305

Reaktionsgleichung

Reaktionsgleichung von HRID 376305
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[C:5]([N:7]1[CH2:12][CH2:11][C:10]([CH2:14]OS(C2C=CC(C)=CC=2)(=O)=O)([F:13])[CH2:9][CH2:8]1)=[O:6].[N-:30]=[N+:31]=[N-:32].[Na+].[N-]=[N+]=[N-].C([N+](CCCC)(CCCC)CCCC)CCC>CS(C)=O>[N:30]([CH2:14][C:10]1([F:13])[CH2:11][CH2:12][N:7]([C:5]([C:4]2[CH:26]=[CH:27][C:28]([F:29])=[C:2]([Cl:1])[CH:3]=2)=[O:6])[CH2:8][CH2:9]1)=[N+:31]=[N-:32]

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 10718129(3-Chloro-4-fluorophenyl)[4-fluoro-4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-piperidinyl]methanone

Produkt 1

HCID 19361720HCID 19361720, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

0.70 g of toluene-4-sulfonic acid 1-(3-chloro-4-fluorobenzoyl)-4-fluoropiperidin-4-yl-methyl ester (1.57 mmol), 0.308 g of sodium azide (4.70 mmol) and 0.20 g of tetrabutylammonium azide (0.70 mmol) are mixed in 3.50 ml of dimethyl sulfoxide. The mixture is heated at 110° C. under a nitrogen atmosphere for 20 hours. The reaction mixture is poured into ice-cold water and then extracted with ethyl acetate. The organic phase is washed with water and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a neutral alumina column (eluent: hexane/ethyl acetate; 70:30). 0.313 g of a yellow oil is obtained.

Aufarbeitung

  1. additionThe reaction mixture is poured into ice-cold water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-96948f1aa17d4d099e8f00b9ae990101
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020345

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