Water → HCID 12853738, compound

HRID 1356641Notes

Reaction equation

HRID 1356641 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([NH:8][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+:21]([O-:23])=[O:22])[CH:5]=1.[Br:24][CH2:25][CH2:26]Br.O>CN(C=O)C>[Br:24][CH2:25][CH2:26][N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:7]1[CH:19]=[CH:20][C:4]([Cl:3])=[CH:5][C:6]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 3691019HCID 3691019, compound

Product 1

HCID 12853738HCID 12853738, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 0.20 g (5.00 mmol)) in DMF (7.0 ml), 4′-chloro-2′-nitro-p-toluenesulfonanilide (1.20 g (3.67 mmol)) was added with stirring at room temperature. To the resulting mixture, after 15 minutes' stirring at room temperature, 1,2-dibromoethane (2.00 ml (23.2 mmol)) was added and the mixture was heated at 130° C. for one hour with stirring. The reaction mixture was cooled to room temperature, poured into water and extracted with diethyl ether. The extract was washed with 1% aqueous sodium hydroxide solution, a saturated sodium chloride solution successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to make the residue crystalline. Hexane was added to the crystals and the crystals were collected while washing to give 1.12 g (70%) 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. temperaturethe mixture was heated at 130° C. for one hour
  4. stirringwith stirring
  5. temperatureThe reaction mixture was cooled to room temperature
  6. extractionextracted with diethyl ether
  7. washThe extract was washed with 1% aqueous sodium hydroxide solution
  8. dry with materiala saturated sodium chloride solution successively, dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. additionHexane was added to the crystals
  11. customthe crystals were collected
  12. washwhile washing

Sources & evidence

ORD record
ord-6a141796f8a649dfa687587d78604f02
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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