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

HRID 2287404Notes

Reaction equation

HRID 2287404 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 18704795N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamideYield 54.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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)-.

Workup

  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

Sources & evidence

ORD record
ord-eb239090278f42fdb30688bd9cd8ea28
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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