Water → 1-[[2-(4-methoxyphenyl)-1,3-oxathiolan-2-yl]methyl]-1H-1,2,4-triazole

HRID 1077877

Reaktionsgleichung

Reaktionsgleichung von HRID 1077877
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:5][CH:4]=1.[SH:17][CH2:18][CH2:19]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(O)CCC.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:10][N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)[S:17][CH2:18][CH2:19][O:16]2)=[CH:5][CH:4]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 15672-MercaptoethanolHCID 6101p-Toluenesulfonic acidHCID 138160051-(4-Methoxyphenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

Produkt 1

HCID 194304951-[[2-(4-methoxyphenyl)-1,3-oxathiolan-2-yl]methyl]-1H-1,2,4-triazoleAusbeute 15,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2631-ButanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a slurry of 32.5 g 1-(4-methoxyphenyl)-2-(1H-1,2,4-triazole-1-yl) ethanone in 500 ml dry toluene and 250 ml 1-butanol was added 23.4 g 2-mercaptoethanol and 38.0 g p-toluenesulfonic acid. The thickened slurry was refluxed under a Dean-Stark trap for about 40 hours, until no more water collected. The solvent was evaporated leaving a solid residue which was dissolved in dichloromethane and washed twice with 10% aqueous sodium hydroxide and once with water. The organic layer was dried, filtered and evaporated to leave an oily residue which partially solidified on high vacuum pumping. The residue was triturated with hot toluene/cyclohexane, cooled and filtered to give 6.5 g of product.

Aufarbeitung

  1. customcollected
  2. customThe solvent was evaporated
  3. customleaving a solid residue which
  4. washwashed twice with 10% aqueous sodium hydroxide and once with water
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customto leave an oily residue which
  9. customThe residue was triturated with hot toluene/cyclohexane
  10. temperaturecooled
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-d0eea0abc0904cec8dc8426575d5c771
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05545655

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