Water → 1-[2-(4-Allyloxy-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazole

HRID 1392227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392227
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[N:13]1([CH2:18][CH2:19]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:17]=[CH:16][N:15]=[N:14]1.[H-].[Na+].O>CN(C=O)C.ClCCl>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12][CH2:19][CH2:18][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 22242087[4-(Prop-2-en-1-yloxy)phenyl]methanethiolHCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate

Produkt 1

HCID 222420761-[2-(4-Allyloxy-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazoleAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

1.58 g (6.14 mmol) (4-allyloxy-phenyl)-methanethiol and 1.64 g (6.14 mmol) toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester were dissolved in 15 ml DMF and cooled to −30° C. 294 mg (12.3 mmol) 95% Sodium hydride were added, the mixture allowed to warm to r.t. and stirred for 12 h. 10 ml Water were added and the residue dissolved in dichloromethane. The organic phase was dried over Na2SO4, solvents removed and the remaining material purified by chromatography on silica gel (ethyl acetate/n-heptane 1:1) to yield 1.33 g (79%) yellow oil.

Aufarbeitung

  1. temperatureto warm to r.t.
  2. dry with materialThe organic phase was dried over Na2SO4, solvents
  3. customremoved
  4. customthe remaining material purified by chromatography on silica gel (ethyl acetate/n-heptane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-16eb1e3942944973aee22fd137a4b4f9
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342030B2

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