Water → HCID 23362005, compound

HRID 1082061Notes

Reaction equation

HRID 1082061 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[F:15][C:16]([F:36])([F:35])[C:17]1[CH:34]=[CH:33][C:20]2[C:21](=O)[NH:22][C:23]3[CH2:31][CH2:30][CH:29]=[CH:28][C:24]=3[S:25](=[O:27])(=[O:26])[C:19]=2[CH:18]=1.O>N1C=CC=CC=1>[F:15][C:16]([F:36])([F:35])[C:17]1[CH:34]=[CH:33][C:20]2[C:21](=[S:2])[NH:22][C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[S:25](=[O:27])(=[O:26])[C:19]=2[CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)2×HCID 23362012HCID 23362012, compound

Product 1

HCID 23362005HCID 23362005, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phosphorus pentasulphide (1 g) was added to a solution of 3-trifluoromethyl-9,10-dihydrodibenzo [b,f][1,4]thiazepin-11-one-5,5dioxide (1 g, 3 mmol) in pyridine (20 ml) and heated under reflux for 6.5 hr. A further 500 mg of phosphorus pentasulphide was added and the mixture heated for a further 6 hr before being allowed to cool overnight. The mixture was added to hot water (100 ml) with stirring. Filtration of the cooled mixture and recrystallisation from ethanol gave the title compound as a yellow solid (650 mg, m.p. 275°-278° C., Rf 0.4, hexane/EtOAc 2:1).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6.5 hr
  3. temperaturethe mixture heated for a further 6 hr
  4. temperatureto cool overnight
  5. filtrationFiltration of the cooled mixture and recrystallisation from ethanol

Sources & evidence

ORD record
ord-a744dff206684ffb93be224b5aad0b2c
Source dataset
uspto-grants-1996_12
Patent number
US05589474

Reaction notes

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