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

HRID 343392Notes

Reaction equation

HRID 343392 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

2M 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 (10ml) 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 (10ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by evaporation
  7. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-2a8a20ddc8fb4f53b6e0df8ce315d81e
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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