Hydrochloric Acid → HCID 18704815, compound

HRID 2287398Notes

Reaction equation

HRID 2287398 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.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1.Cl>COCCOC.O>[Br:12][C:7]1[N:8]=[C:9]([O:10][CH3:11])[C:4]([NH:3][S:26]([C:21]2[C:20]([C:17]3[CH:16]=[CH:15][C:14]([CH3:13])=[CH:19][CH:18]=3)=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:28])=[O:27])=[N:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 33884482-(4-methylphenyl)benzenesulfonyl ChlorideHCID 113447242-Amino-5-bromo-3-methoxypyrazine

Product 1

HCID 18704815HCID 18704815, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Sodium hydride (oil free; 0.053 g) was added to a solution of 2-amino-5-bromo-3-methoxypyrazine (0.151 g) in DME (5 ml). The solution was stirred for 10 minutes and then a solution of 4'-methyl-2-biphenylsulphonyl chloride (0.198 g) in DME (2 ml) was added. The solution was allowed to stand for 1 hour and then water (25 ml) was added. 2M Hydrochloric acid (2 ml) was added and the mixture was extracted eith ethyl acetate (2×25 ml). The extracts were washed with water (25 ml) and saturated sodium chloride solution (25 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was recrystallised from ethyl acetate to give N-(5-bromo-3-methoxy-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide (0.12 g) m.p. 204-206° C.; 1H NMR (d6 -DMSO): 2.4 (s,3H), 3.85(s,3H), 7.05-7.2(m,4H), 7.3(dd,1H), 7.55-7.7(m,2H), 7.8(s,1H), 8.1(dd,1H); mass spectrum (+ve FAB, methanol/NBA): 436 (M+H)+.

Workup

  1. waitto stand for 1 hour
  2. extractionthe mixture was extracted eith ethyl acetate (2×25 ml)
  3. washThe extracts were washed with water (25 ml) and saturated sodium chloride solution (25 ml)
  4. dry with materialdried (MgSO4)
  5. customVolatile material was removed by evaporation
  6. customthe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-4906586bc9cc4baea5c8a1c26d6b47cc
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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