5-Phenyl-1,3,4-oxadiazole-2-thiol → HCID 22557305, Verbindung

HRID 984053

Reaktionsgleichung

Reaktionsgleichung von HRID 984053
[Cl:1][C:2]1[CH:3]=[C:4]([N:18]2[C:23](=[O:24])[NH:22][C:21](=[O:25])[CH:20]=[N:19]2)[CH:5]=[C:6]([Cl:17])[C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)O.[C:26]1([C:32]2[O:36][C:35](=[S:37])[NH:34][N:33]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:18]2[C:23](=[O:24])[NH:22][C:21](=[O:25])[CH:20]=[N:19]2)[CH:5]=[C:6]([Cl:17])[C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[S:37][C:35]1[O:36][C:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:33][N:34]=1

Komponenten

4

Edukt 2

HCID 7352545-Phenyl-1,3,4-oxadiazole-2-thiolHCID 22557401HCID 22557401, Verbindung

Produkt 1

HCID 22557305HCID 22557305, VerbindungAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6395Methanesulfonic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-[3,5-dichloro-4-[(4-chlorophenyl)hydroxymethyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.005 mol) and 5-phenyl-1,3,4-oxadiazole-2(3H)-thione (0.006 mol) in methanesulfonic acid (20 ml) was stirred for 18 hours at RT. The reaction mixture was poured out into water/ice (150 ml), and the resulting precipitate was filtered off, stirred in water, treated with NaHCO3 and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97.5/2.5). The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE, filtered off and dried, yielding 1 g of (±)-2-[3,5-dichloro-4-[(4-chlorophenyl)[(5-phenyl-1,3,4-oxadiazol-2-yl)thio]methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (comp. 406).

Aufarbeitung

  1. filtrationthe resulting precipitate was filtered off
  2. stirringstirred in water
  3. additiontreated with NaHCO3
  4. extractionthis mixture was extracted with CH2Cl2
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by flash column chromatography over silica gel (eluent: CH2Cl2/CH3OH 97.5/2.5)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. stirringThe residue was stirred in DIPE
  12. filtrationfiltered off
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f5e4b57e8f3f4629802b8fb444ca59f2
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867207B2

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