Sodium Sulfate → 2,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine

HRID 1079320Notes

Reaction equation

HRID 1079320 reaction equation
[S:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][NH:4][C:3](=O)[CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[S:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 41786501,4-Benzothiazepin-3(2H)-one, 4,5-dihydro-HCID 21226445Aluminium lithium hydride2×

Product 1

HCID 122691062,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,5-Dihydro-1,4-benzothiazepin-3(2H)-one (12 g, prepared in a similar manner to example 1 of international patent application WO 92/21668) was added to a stirred solution of lithium aluminium hydride (6.3 g) in dry tetrahydrofuran (400 ml). After the addition, the reaction mixture was heated under reflux for ten minutes and cooled. Excess of lithium aluminium hydride was decomposed by adding a saturated aqueous solution of sodium sulphate. The mixture was filtered and the solvent was removed from the filtrate by evaporation to give 2,3,4,5-tetrahydro-1,4-benzothiazepine as an oil which was used without further purification. Yield 9.4 g.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for ten minutes
  4. temperaturecooled
  5. filtrationThe mixture was filtered
  6. customthe solvent was removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-47c471b4a2c34b53b79ea88bd9ca15e8
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

Loading…