Water → HCID 18509244, compound

HRID 1356646Notes

Reaction equation

HRID 1356646 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:21]=[CH:20][C:7]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[C:6]([N+:22]([O-:24])=[O:23])[CH:5]=1.[CH3:25][CH2:26][CH2:27]Br.O>CN(C=O)C>[CH3:19][N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:10])=[O:11])[C:7]1[CH:20]=[CH:21][C:4]([O:3][CH2:25][CH2:26][CH3:27])=[CH:5][C:6]=1[N+:22]([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 18509211HCID 18509211, compound

Product 1

HCID 18509244HCID 18509244, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.05 g (1.25 mmol)) in 1.0 ml of DMF, 4′-hydroxy-N-methyl-2′-nitro-p-toluenesulfonanilide (0.32 g (0.99 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, n-propyl bromide (0.20 g (2.20 mmol)) was added dropwise and the mixture was stirred at room temperature for 15 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. Diisopropyl ether was added to the residue and crystals separated were filtered and washed to give 0.15 g (42%) of the title compound as pale yellow crystals.

Workup

  1. additionwas added
  2. stirringTo the resulting mixture, after 15 minutes' stirring at room temperature
  3. stirringthe mixture was stirred at room temperature for 15 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionDiisopropyl ether was added to the residue and crystals
  9. customseparated
  10. filtrationwere filtered
  11. washwashed

Sources & evidence

ORD record
ord-e137f5cc1f0f48e98af3cb2997c37901
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

Loading…