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

HRID 2287399Notes

Reaction equation

HRID 2287399 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-ff04971656434b31931f1182a2f7d286
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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