Dansyl chloride → HCID 18704816, compound

HRID 2287373Notes

Reaction equation

HRID 2287373 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([Br:10])=[N:8][C:7]([Br:11])=[CH:6][N:5]=1.[H][H].[CH3:14][N:15]([CH3:30])[C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[C:21]2[S:26](Cl)(=[O:28])=[O:27]>CN(C)C=O>[CH3:14][N:15]([CH3:30])[C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[C:21]2[S:26]([NH:3][C:4]1[C:9]([Br:10])=[N:8][C:7]([Br:11])=[CH:6][N:5]=1)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 11801Dansyl chlorideHCID 24758Sodium hydrideHCID 6200042-Amino-3,5-dibromopyrazineHCID 178418361HCID 178418361, compound

Product 1

HCID 18704816HCID 18704816, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Sodium hydride (60% dispersion in oil; 0.16 g) was added to a solution of 2-amino-3,5-dibromopyrazine (0.506 g) in N,N-dimethylformamide (30 ml). When evolution of hydrogen ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (0.54 g) was added and the solution was heated at 95° C. for 18 hours. Volatile material was removed by evaporation and water (50 ml) was added to the residue. The mixture was extracted with ethyl acetate (20 ml), and the aqueous layer was neutralised with 0.05M aqueous acetic acid (40 ml) and extracted with ethyl acetate (3×25 ml). The extracts were washed with water (20 ml) and saturated sodium chloride solution (20 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by elution with dichloromethane through a silica gel mega Bond Elut column. The resulting foam was triturated with ether/hexane (1:1 v/v) to give 5-(dimethylamino)-N-(3,5-dibromo-2-pyrazinyl)-1-naphthalenesulphonamide, (0.052 g), m.p. 178° C.; mass spectrum (+ve FAB, methanol/NBA): 485 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation and water (50 ml)
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate (20 ml)
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. washThe extracts were washed with water (20 ml) and saturated sodium chloride solution (20 ml)
  6. dry with materialdried (MgSO4)
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified by elution with dichloromethane through a silica gel mega Bond Elut column
  9. customThe resulting foam was triturated with ether/hexane (1:1 v/v)

Sources & evidence

ORD record
ord-57356eb10e404759a4ceab0c75e83a84
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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