Hydrochloric Acid → Dibenzo[b,f][1,4]thiazepine-11(10H)-thione

HRID 1082064Notes

Reaction equation

HRID 1082064 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH:15]1[C:20]2[C:21](=O)[NH:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[S:25][C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl>N1C=CC=CC=1>[CH:15]1[C:20]2[C:21](=[S:2])[NH:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[S:25][C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14817Phosphorus sulfide (P2S5)HCID 374829Dibenzothiazepinone

Product 1

HCID 667552Dibenzo[b,f][1,4]thiazepine-11(10H)-thione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phosphorus pentasulphide (1.2 eq) was added to a solution of 10,11-dihydrodibenzo[b,f][1,4]thiazepin-11-one (1.14 g, 5 mmol) in pyridine (40 ml) and heated under reflux for 15 hr. The mixture was allowed to cool and poured into hydrochloric acid (1.3M) at 0° C. Filtration of the yellow precipitate and purification by chromatography on silica (eluting with dichloromethane/methanol, 99:1) followed by recrystallisation from ethanol gave the title compound as yellow crystals (700 mg, m.p. 245°-246° C., Rf 0.81, CH2Cl2/MeOH9:1).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 hr
  3. temperatureto cool
  4. filtrationFiltration of the yellow precipitate and purification by chromatography on silica (eluting with dichloromethane/methanol, 99:1)
  5. customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-98462676614b4174ba429cf321c63b5c
Source dataset
uspto-grants-1996_12
Patent number
US05589474

Reaction notes

Loading…