O-Xylene → HCID 14118983, compound

HRID 974810Notes

Reaction equation

HRID 974810 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=1[C:11]#[N:12].[OH-:20].[Na+].C1(C)C(C)=CC=CC=1>C(O)(=O)C.S(=O)(=O)(O)O.O>[N+:17]([C:14]1[CH:15]=[CH:16][C:9]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:12][C:11](=[O:20])[C:10]=2[CH:13]=1)([O-:19])=[O:18]

Participants

7

Reactant 3

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 19969463HCID 19969463, compound

Product 1

HCID 14118983HCID 14118983, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

2-(2-Aminophenylthio)-5-nitrobenzonitrile (8.5 g, 25 mmol) was dissolved in a mixture of glacial acetic acid (80 ml), concentrated sulphuric acid (100 ml) and water (80 ml) and then heated under reflux for 6 hours. The cooled mixture was added to ice water (500 ml) and brought to pH 4 by addition of 10N aqueous sodium hydroxide. Extraction with dichloromethane followed by filtration, drying (sodium sulphate) and evaporation of the organic layer afforded a residue which was put into xylene (500 ml) and refluxed for 15 hours with azeotropic removal of water. On cooling a brown powder deposited which was filtered off and purified by chromatography on silica gel eluting with 1:1 v/v ethyl acetate-hexane. Recrystallisation from ethanol gave the product as a greyish powder (2.80 g, m/s, M+ =272).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. extractionExtraction with dichloromethane
  4. filtrationfollowed by filtration
  5. customdrying
  6. custom(sodium sulphate) and evaporation of the organic layer
  7. customafforded a residue which
  8. temperatureOn cooling a brown powder
  9. filtrationwas filtered off
  10. custompurified by chromatography on silica gel eluting with 1:1 v/v ethyl acetate-hexane
  11. customRecrystallisation from ethanol
  12. customgave the product as a greyish powder (2.80 g, m/s, M+ =272)

Sources & evidence

ORD record
ord-2f6522ab89514f5288862e1ce463c366
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Reaction notes

Loading…