Acetic Acid → Dibenzothiazepinone

HRID 1082063Notes

Reaction equation

HRID 1082063 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][CH:14]=[CH:13][C:10]=1[C:11]#[N:12].C(O)(=[O:19])C.S(=O)(=O)(O)O.[OH-].[Na+]>O>[CH:13]1[C:10]2[C:11](=[O:19])[NH:12][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8][C:9]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 3662332-(2-Aminophenyl)sulfanylbenzonitrile

Product 1

HCID 374829Dibenzothiazepinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-Aminophenylthio)benzonitrile (3.72 g, 16 mmol) was dissolved in water (35 ml), acetic acid (35 ml) and concentrated sulphuric acid (35 ml) and stirred and heated under reflux for 3 hr. The mixture was allowed to cool and poured onto crushed ice (600 ml) and adjusted to pH 6 with sodium hydroxide solution (10N). The product was extracted into dichloromethane (700 ml), dried (MgSO4) and evaporated in vacuo. The residue was dissolved in xylene (250 ml) and refluxed in a Dean-Stark apparatus for 72 hr. Filtration of the cold reaction mixture and recrystallisation from ethanol gave the title compound as a white crystals (2.99 g, m.p. 255°-256° C., Rf 0.68, CH2Cl2 /MeOH 19:1).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hr
  3. temperatureto cool
  4. additionpoured
  5. extractionThe product was extracted into dichloromethane (700 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. dissolutionThe residue was dissolved in xylene (250 ml)
  9. temperaturerefluxed in a Dean-Stark apparatus for 72 hr
  10. filtrationFiltration of the cold reaction mixture and recrystallisation from ethanol

Sources & evidence

ORD record
ord-0da86f0c8ae04968bcc3f78073463e58
Source dataset
uspto-grants-1996_12
Patent number
US05589474

Reaction notes

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