Dimethyl Sulfoxide → 4-(Benzoxazol-2-yl)benzylazide

HRID 1734690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734690
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.[N-:18]=[N+:19]=[N-:20].[Na+].CS(C)=O>C1COCC1.C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:18]=[N+:19]=[N-:20])=[CH:12][CH:11]=1

Komponenten

6

Edukt 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 110335154-(Benzoxazol-2-yl)benzyl bromide

Produkt 1

HCID 194207644-(Benzoxazol-2-yl)benzylazide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(benzoxazol-2-yl)benzyl bromide (0.49 g; 1.7 mmol) in THF (3 ml) is added sodium azide (0.22 g; 3.4 mmol) and dimethylsulfoxide (1 ml). The reaction is stirred for 24 hours and diluted with CH2Cl2, washed with H2O 3x and brine, dried (MgSO4) and concentrated in vacuo. The product is purified by column chromatography using 50% CH2Cl2 /petroleum ether to yield 4-(benzoxazol-2-yl)benzylazide as a white solid which is used directly in Step B.

Aufarbeitung

  1. washwashed with H2O 3x and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8816979c7dcf48eb83713fa108d6df46
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534532

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