Hydrochloric Acid → 2-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)yl)phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetic acid

HRID 1072479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072479
C([O:3][C:4](=[O:36])[CH2:5][C:6]1[S:10][C:9]([C:11]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([N:21]3[C:26](=[O:27])[NH:25][C:24](=[O:28])[CH:23]=[N:22]3)=[CH:16][C:15]=2[Cl:29])([CH3:13])[CH3:12])=[N:8][C:7]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)C.[OH-].[Na+].Cl.CCOC(C)=O>CO.C1COCC1>[Cl:20][C:19]1[CH:18]=[C:17]([N:21]2[C:26](=[O:27])[NH:25][C:24](=[O:28])[CH:23]=[N:22]2)[CH:16]=[C:15]([Cl:29])[C:14]=1[C:11]([C:9]1[S:10][C:6]([CH2:5][C:4]([OH:36])=[O:3])=[C:7]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:8]=1)([CH3:13])[CH3:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 9828866ethyl-2-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl]phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetate

Produkt 1

HCID 158708342-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)yl)phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetic acidAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of intermediate (9) (0.00183 mole) and NaOH 1N (0.0055 mole) in CH3OH (25 ml) and THF (25 ml) was stirred overnight at RT. The reaction mixture was acidified with 1N HCl (8 ml) and the resulting product was taken up into EtOAc. The organic layer was washed with brine, dried, filtered and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off, washed with DIPE, and dried, yielding 0.8 g (79%) of 2-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)yl)phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetic acid (intermediate 10).

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. customdried
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was crystallized from CH3CN
  6. filtrationThe precipitate was filtered off
  7. washwashed with DIPE
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-64ad69748b0a4f4bbe279672e67e234e
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911444B2

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