8-chlorodibenzo[b,f][1,4]thiazepin-11(10H)-one → 8-Chloro-10,11-dihydrodibenzo[b,f][1,4]thiazepine

HRID 275310Notes

Reaction equation

HRID 275310 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=O)[NH:10][C:4]=2[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 8271058-chlorodibenzo[b,f][1,4]thiazepin-11(10H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 542201108-Chloro-10,11-dihydrodibenzo[b,f][1,4]thiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5.23 g (20 mmol) of 8-chlorodibenzo[b,f][1,4]thiazepin-11(10H)-one (34), prepared in the manner described above in Example 34, in 175 mL of THF cooled in an ice bath is added dropwise 100 mL of M lithium aluminum hydride solution. The reaction is heated at reflux for 4 hours. The reaction is quenched by the addition of 3.8 mL of 15% NaOH and 15.2 mL of H2O. The reaction mixture is filtered through a pad of celite. The filtrate is concentrated in vacuo and is recrystallized from cyclohexane.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureThe reaction is heated
  3. temperatureat reflux for 4 hours
  4. customThe reaction is quenched by the addition of 3.8 mL of 15% NaOH and 15.2 mL of H2O
  5. filtrationThe reaction mixture is filtered through a pad of celite
  6. concentrationThe filtrate is concentrated in vacuo
  7. customis recrystallized from cyclohexane

Sources & evidence

ORD record
ord-ba24e78c69ff4bf18f30ea1783da9816
Source dataset
uspto-grants-1995_02
Patent number
US05393747

Reaction notes

Loading…