Water → HCID 19969454, compound

HRID 974807Notes

Reaction equation

HRID 974807 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:4]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=2[NH2:19])=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#N.O.S(=O)(=O)(O)[OH:24].[OH-].[Na+]>C(O)(=O)C>[CH3:18][C:14]1[C:13]2[NH:19][C:6](=[O:24])[C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:21])([F:20])[F:1])[C:4]=3[S:11][C:12]=2[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 53909561HCID 53909561, compound

Product 1

HCID 19969454HCID 19969454, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Trifluoromethyl-2-(3-methyl-2-aminophenylthio) benzonitrile (2.53 g, 8 mmol) was dissolved in acetic acid (25 ml), water (25 ml) and concentrated sulphuric acid (25 ml) and the mixture stirred and heated under reflux for 7.5 hours, then at ambient temperature for 15 hours before further sulphuric acid (25 ml) was added and the mixture stirred and heated under reflux for a further 8.5 hours. The mixture was allowed to stand at ambient temperature overnight then poured onto crushed ice (200 ml) and basified to pH 4 with aqueous sodium hydroxide (10N). The mixture was extracted with dichloromethane (3×200 ml) and the combined organic fractions dried (magnesium sulphate) and evaporated. The residue was dissolved in xylene (400 ml) and heated under reflux for 72 hours in a Dean-Stark apparatus, before being allowed to cool. After evaporation of the xylene, recrystallisation from toluene, followed by recrystallisation from ethanol, the title compound was obtained as an off-white solid (1.02 g, m.p. 273°-277°).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 7.5 hours
  3. temperatureheated
  4. temperatureunder reflux for a further 8.5 hours
  5. additionthen poured
  6. extractionThe mixture was extracted with dichloromethane (3×200 ml)
  7. dry with materialthe combined organic fractions dried (magnesium sulphate)
  8. customevaporated
  9. dissolutionThe residue was dissolved in xylene (400 ml)
  10. temperatureheated
  11. temperatureunder reflux for 72 hours in a Dean-Stark apparatus
  12. temperatureto cool
  13. customAfter evaporation of the xylene, recrystallisation from toluene
  14. customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-c0a9ba9443e84931ba6c3b1d92564da1
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Reaction notes

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