Sodium hydride → HCID 19039999, compound

HRID 1684562Notes

Reaction equation

HRID 1684562 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:19])[C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[C:10]2[S:15]([NH2:18])(=[O:17])=[O:16].[H][H].Cl[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1>CN(C)C=O>[CH3:3][N:4]([CH3:19])[C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[C:10]2[S:15]([NH:18][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1)(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 65077DansylamideHCID 783082-Chloro-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 19039999HCID 19039999, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Sodium hydride (60% dispersion in oil; 160 mg) was added to a solution of 5-dimethylamino-1-naphthalenesulphonamide (500 mg) in N,N-dimethylformamide (30 ml). When evolution of hydrogen ceased, 2-chloro-5-nitropyridine (317 mg) 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-(5-nitro-2-Pyridyl)-1-naphthalenesulphonamide (60 mg), m.p. 196° C.; mass spectrum (+ve FAB, methanol/NBA): 373 (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-ecc0d0efa12b4e17867213e9e50bd210
Source dataset
uspto-grants-1997_06
Patent number
US05641793

Reaction notes

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