Sodium Hydroxide → N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide

HRID 2287404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2287404
[OH-].[Na+].C(OC([N:10]([C:27]1[C:32]([O:33][CH3:34])=[N:31][C:30]([CH3:35])=[CH:29][N:28]=1)[S:11]([C:14]1[C:15]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])=O)C(C)C>CO.C(COC)OC>[CH3:34][O:33][C:32]1[C:27]([NH:10][S:11]([C:14]2[C:15]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[N:28][CH:29]=[C:30]([CH3:35])[N:31]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 18704823N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide

Produkt 1

HCID 18704795N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamideAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2 M Sodium hydroxide solution (0.6 ml) was added to a solution of N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide (0.232 g) in methanol (2.4 ml) and dimethoxyethane (2.4 ml) and the mixture was stirred for 2 hours. Volatile material was removed by evaporation and water (10 ml) was added to the residue. The mixture was acidified with 2M hydrochloric acid and extracted with ethyl acetate (2×10 ml). The extracts were washed with water (10 ml) and saturated sodium chloride solution (10 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue was recrystallised from ethanol to give N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide (0.1 g) m.p. 184-185° C.; 1H NMR (d6 -DMSO): 2.3 (s,3H), 2.4 (s,3H), 3.6 (s,3H), 7.05-7.3 (m,5H), 7.45-7.7 (m,3H), 8.1 (dd,1H), 9.35-9.45 (br s,1H); mass spectrum (-ve FAB, DMSO/Methanol/GLY): 368 (M-H)-.

Aufarbeitung

  1. customVolatile material was removed by evaporation and water (10 ml)
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. washThe extracts were washed with water (10 ml) and saturated sodium chloride solution (10 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by evaporation
  7. customthe residue was recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-eb239090278f42fdb30688bd9cd8ea28
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06083951

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