Dansyl chloride → HCID 10646616, compound

HRID 343368Notes

Reaction equation

HRID 343368 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13](Cl)(=[O:15])=[O:14].[NH2:18][C:19]1[C:24]([O:25][CH3:26])=[N:23][C:22]([Br:27])=[CH:21][N:20]=1>N1C=CC=CC=1>[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13]([NH:18][C:19]1[C:24]([O:25][CH3:26])=[N:23][C:22]([Br:27])=[CH:21][N:20]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 11801Dansyl chlorideHCID 113447242-Amino-5-bromo-3-methoxypyrazine

Product 1

HCID 10646616HCID 10646616, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

5-Dimethylamino-1-naphthalenesulphonyl chloride (15.2 g) and 2-amino-5-bromo-3-methoxypyrazine (obtained as described in Gazz. Chim. Ital. 1960, 90, 1807) (9.5 g) were mixed intimately in a mortar and pestle and added to pyridine (150 ml) at 0° C. The solution was kept at 0° C. for 1 hour and then heated at 80° C. for 18 hours. Volatile material was removed by evaporation and dichloromethane (250 ml) was added to the residue. Insoluble material was removed by filtration and the filtrate was washed with water (100 ml) and saturated sodium chloride solution (100 ml). The solution was treated with charcoal and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:4 v/v). The resulting solid was triturated with ether and recrystallised from ethanol to give 5-dimethylamino-N-(5-bromo-3-methoxy-2-pyrazinyl)-1-naphthalenesulphonamide (4.7 g), m.p. 166°-167° C.; 1H NMR (d6 -DMSO): 2.8 (s,6H), 3.9 (s,3H), 7.2 (d,1H), 7.55-7.7 (d,2H), 7.8 (s,1H), 8.3 (d,1H), 8.4-8.5 (m,2H), 11.5 (s,1H); mass spectrum (+ve CI): 437 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation and dichloromethane (250 ml)
  2. additionwas added to the residue
  3. customInsoluble material was removed by filtration
  4. washthe filtrate was washed with water (100 ml) and saturated sodium chloride solution (100 ml)
  5. additionThe solution was treated with charcoal
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed by evaporation
  8. customthe residue was purified by flash chromatography
  9. washeluting with ethyl acetate/hexane (1:4 v/v)
  10. customThe resulting solid was triturated with ether
  11. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-e5e6a276d85a4793814838fd4c543719
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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