Sodium Sulfate → 6-Chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

HRID 1079317Notes

Reaction equation

HRID 1079317 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][NH:9][C:10](=O)[CH2:11][S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:7]2[CH2:8][NH:9][CH2:10][CH2:11][S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 102200036-Chloro-4,5-dihydro-1,4-benzothiazepin-3(2H)-oneHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 101981056-Chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-4,5-dihydro-1,4-benzothiazepin-3(2H)-one (9.8 g, prepared in a similar manner to example 11 of international patent application WO 92/21668) was added to a stirred solution of lithium aluminium hydride (5.01 g) in dry tetrahydrofuran (400 ml). After the addition, the reaction mixture was heated under reflux for five minutes and then cooled. Excess lithium aluminium hydride was decomposed by adding of a saturated aqueous solution of sodium sulphate. The mixture was filtered and the solvent evaporated from the filtrate to give 6-chloro-2,3,4,5-tetrahydro-1,4-benzothiazepine as an oil.

Workup

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

Sources & evidence

ORD record
ord-cea44638fda74d37bea625e0b91b47d3
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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