Hydrochloric Acid → HCID 20392271, compound

HRID 1863168Notes

Reaction equation

HRID 1863168 reaction equation
[CH3:1][C:2]1[C:17]([CH3:18])=[CH:16][C:5]2[N:6]([CH3:15])[C:7](=O)[C:8]3[C:9](=[CH:11][S:12][CH:13]=3)[NH:10][C:4]=2[CH:3]=1.B.Cl.[OH-].[Na+]>O1CCCC1.O.CO>[CH3:1][C:2]1[C:17]([CH3:18])=[CH:16][C:5]2[N:6]([CH3:15])[CH2:7][C:8]3[C:9](=[CH:11][S:12][CH:13]=3)[NH:10][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6331BoraneHCID 14798Sodium HydroxideHCID 20392247HCID 20392247, compound

Product 1

HCID 20392271HCID 20392271, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 3.88 g. of 4,9-dihydro-6,7,9-trimethyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of tetrahydrofuran, cooled in an ice bath and stirred under argon is added 60 ml. of 1 M borane in tetrahydrofuran, dropwise over 15 minutes. The mixture is stirred for one hour at room temperature, refluxed for 18 hours, cooled in an ice bath and decomposed by the addition of 30 ml. of 6 N hydrochloric acid. The mixture is stirred for one hour, 30 ml. of 10 N sodium hydroxide is added, stirring is continued for one hour and the tetrahydrofuran is evaporated. The remaining aqueous layer is filtered giving blue tinted crystals. These crystals are combined with 125 ml. of absolute methanol and saturated with gaseous hydrogen chloride. A 25 ml. portion of water is added and the mixture is heated on a steam bath until solution is complete. The methanol is evaporated in vacuo, 150 ml. of water is added and the solution is made basic with 10 N sodium hydroxide. The solution is extracted with methylene chloride and the extract is dried over magnesium sulfate and evaporated giving the desired product as blue crystals, mp. 121°-125° C.

Workup

  1. additionis added 60 ml
  2. stirringThe mixture is stirred for one hour at room temperature
  3. temperaturerefluxed for 18 hours
  4. temperaturecooled in an ice bath
  5. additiondecomposed by the addition of 30 ml
  6. stirringThe mixture is stirred for one hour
  7. stirringstirring
  8. customthe tetrahydrofuran is evaporated
  9. filtrationThe remaining aqueous layer is filtered
  10. customgiving blue
  11. temperaturethe mixture is heated on a steam bath until solution
  12. customThe methanol is evaporated in vacuo, 150 ml
  13. additionof water is added
  14. extractionThe solution is extracted with methylene chloride
  15. dry with materialthe extract is dried over magnesium sulfate
  16. customevaporated

Sources & evidence

ORD record
ord-0026bf9bf5c44083bae75594d30d1c12
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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