Sodium Bicarbonate → HCID 18509285, compound

HRID 1356696Notes

Reaction equation

HRID 1356696 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[C:4]([N+:20]([O-])=O)[CH:3]=1.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:20][C:4]1[CH:3]=[C:2]([Cl:1])[CH:19]=[CH:18][C:5]=1[N:6]([CH3:17])[S:7]([C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18509311HCID 18509311, compound

Product 1

HCID 18509285HCID 18509285, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4′-chloro-N-methyl-2′-nitro-p-toluenesulfonanilide (7.11 g (20.9 mmol)), stannous chloride (14.7 g (62.6 mmol)) and ethanol (100.0 ml) was stirred at room temperature for 45 minutes, and at 50° C. for 16 hours. After being allowed to cool to room temperature, the reaction mixture was neutralized with a saturated aqueous solution of sodium bicarbonate and the insolubles were removed by filtration. The filtrate was extracted with ethyl acetate and the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with acetone-chloroform-hexane (1:3:5) as eluent to give 5.22 g (81%) of the title compound as white crystals.

Workup

  1. waitat 50° C. for 16 hours
  2. temperatureto cool to room temperature
  3. customthe insolubles were removed by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f345df175c04ed39f1de8ed2bef63e4
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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