Hydrochloric Acid → N-(5-bromo-3-methoxy-2-pyrazinyl)-2-biphenylsulphonamide

HRID 343387Notes

Reaction equation

HRID 343387 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([O:10][CH3:11])=[N:8][C:7]([Br:12])=[CH:6][N:5]=1.[C:13]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:16]=[CH:17][CH:18]=1.Cl>C(COC)OC.O>[Br:12][C:7]1[N:8]=[C:9]([O:10][CH3:11])[C:4]([NH:3][S:19]([C:14]2[C:13]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:21])=[O:20])=[N:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 27566802-Phenylbenzene-1-sulfonyl chlorideHCID 113447242-Amino-5-bromo-3-methoxypyrazine

Product 1

HCID 18704821N-(5-bromo-3-methoxy-2-pyrazinyl)-2-biphenylsulphonamideYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (60% dispersion in oil; 0.198 g) was suspended in dimethoxyethane (5 ml) and 2-amino-5-bromo-3-methoxypyrazine (0.405 g) was added with stirring. After 15 minutes, 2-biphenylsulphonyl chloride (0.5 g) was added and the mixture was stirred for 18 hours. The reaction mixture was poured into water (20 ml) and acidified to pH2 with concentrated hydrochloric acid and extracted with ethyl acetate (3×25 ml). The combined organic extracts were evaporated and the residue was purified by flash chromatography on silica gel (30 g), eluting with hexane/ethyl acetate/glacial acetic acid (160/40/1 v/v), to give N-(5-bromo-3-methoxy-2-pyrazinyl)-2-biphenylsulphonamide (0.46 g); 1H NMR (d6 -DMSO): 3.82(s,3H), 7.2-7.4(m,6H), 7.53-7.7(m,2H), 7.78(s,1H), 8.08(dd,1H), 10.33(br,1H); mass spectrum (+ve FAB, methanol/NBA): 420(M+H)+.

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. extractionextracted with ethyl acetate (3×25 ml)
  3. customThe combined organic extracts were evaporated
  4. customthe residue was purified by flash chromatography on silica gel (30 g)
  5. washeluting with hexane/ethyl acetate/glacial acetic acid (160/40/1 v/v)

Sources & evidence

ORD record
ord-8176d8a3f9d94ca7abd636d592b10c08
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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