Water → HCID 18509258, compound

HRID 1356642Notes

Reaction equation

HRID 1356642 reaction equation
[H-].[Na+].N1C=NC=N1.Br[CH2:9][CH2:10][N:11]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].O>CN(C=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N:11]([CH:10]=[CH2:9])[S:22]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)(=[O:24])=[O:23])=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 12853738HCID 12853738, compound

Product 1

HCID 18509258HCID 18509258, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.04 g (1.00 mmol)) in DMF (5.0 ml), 1,2,4-triazole (0.08 g (1.16 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, N-(2-bromoethyl)-4′-chloro-2′-nitro-p-toluenesulfonanilide (0.35 g (0.81 mmol)) was added and the mixture was stirred at room temperature for 18 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. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:3) as eluent, to give 0.052 g (18%) 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 18 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

Sources & evidence

ORD record
ord-5f802989fb1b4c43a1b874cbe91796d8
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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