Sodium hydride → 1-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazole

HRID 892259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892259
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[C:7]([CH3:13])[CH:6]=1)[CH:2]=[CH2:3].[N:14]1([CH2:19][CH2:20]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:18]=[CH:17][N:16]=[N:15]1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12][CH2:20][CH2:19][N:14]2[CH:18]=[CH:17][N:16]=[N:15]2)=[C:7]([CH3:13])[CH:6]=1)[CH:2]=[CH2:3]

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 22242072(4-Allyloxy-2-methyl-phenyl)-methanethiolHCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate

Produkt 1

HCID 222420831-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazoleAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a mixture of 1.98 g (10.2 mmol) (4-allyloxy-2-methyl-phenyl)-methanethiol and 2.72 g (10.2 mmol) toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester in 25 ml N,N-dimethylformamide was added under argon at −50° C. 515 mg (20.4 mmol) sodium hydride. The mixture was allowed to warm up to room temperature and was stirred under argon for 12 hours. 80% of the DMF was stilled off in vacuo, ethyl acetate and water given to the mixture. The aqueous phase was reextracted with ethyl acetate and the combined organic extracts dried and evaporated to yield 2.8 g of 1-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazole as brown oil. The raw material (73% purity) was used without further purification.

Aufarbeitung

  1. additionwas added under argon at −50° C
  2. customthe combined organic extracts dried
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cd96bc8283bc4b05a80a37544652ec7f
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005526B2

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