Hydrochloric Acid → HCID 19902357, compound

HRID 2372814Notes

Reaction equation

HRID 2372814 reaction equation
N([O-])=O.[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18](N)=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.Cl.C(OC([S-])=[S:27])C.[K+]>O.C(OCC)(=O)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([SH:27])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 572814BENZENAMINE, 4-[(4-FLUOROPHENYL)SULFONYL]-HCID 2735045Potassium ethylxanthateHCID 23668193Sodium Nitrite

Product 1

HCID 19902357HCID 19902357, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A solution of sodium nitrite (302 mg in 1 ml of water) is added to a suspension of 1 g (0.00398 mol) of 4-[(4-fluorophenyl)sulfonyl]benzeneamine in a solution of hydrochloric acid (1.68 ml of concentrated hydrochloric acid in 5 ml of water) at 5° C. After stirring for 5 minutes, this solution is added dropwise to a solution of 2.47 g of potassium ethylxanthate in 5 ml of water at 70° C. The reaction mixture is diluted with ethyl acetate. The organic phase is washed with a 1 N solution of sodium hydroxide and a saturated solution of sodium chloride and then dried over magnesium sulfate. After evaporation of the solvents, the residue is taken up in 15 ml of ethanol. 1.47 g of potassium hydroxide are added and the reaction mixture is heated at 45° C. for 10 minutes. It is then poured into iced water and partially purified by extraction with ethyl acetate. The aqueous phase, cooled with ice, is rendered acidic by the addition of concentrated hydrochloric acid and is then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and the solvents are evaporated off to dryness. 640 mg (yield: 60%) of the expected product are thus obtained.

Workup

  1. washThe organic phase is washed with a 1 N solution of sodium hydroxide
  2. dry with materiala saturated solution of sodium chloride and then dried over magnesium sulfate
  3. customAfter evaporation of the solvents
  4. addition1.47 g of potassium hydroxide are added
  5. additionIt is then poured into iced water
  6. custompartially purified by extraction with ethyl acetate
  7. temperatureThe aqueous phase, cooled with ice
  8. additionis rendered acidic by the addition of concentrated hydrochloric acid
  9. extractionis then extracted with ethyl acetate
  10. dry with materialThe organic phase is dried over magnesium sulfate
  11. customthe solvents are evaporated off to dryness

Sources & evidence

ORD record
ord-46424a7583a54310847618405366f62b
Source dataset
uspto-grants-1992_03
Patent number
US05100913

Reaction notes

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