Hydrochloric Acid → HCID 20392262, compound

HRID 1863183Notes

Reaction equation

HRID 1863183 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]2[NH:8][C:9](=O)[C:10]3[C:11](=[CH:13][S:14][CH:15]=3)[NH:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].B.Cl>O1CCCC1>[N+:1]([C:4]1[CH:18]=[CH:17][C:7]2[NH:8][CH2:9][C:10]3[C:11](=[CH:13][S:14][CH:15]=3)[NH:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 20392246HCID 20392246, compound

Product 1

HCID 20392262HCID 20392262, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An 8 g. portion of 4,9-dihydro-6-nitro-10H-thieno [3,4-b][1,5]benzodiazepin-10-one in 155 ml. of tetrahydrofuran is stirred, under nitrogen, with cooling in an ice bath. To this is added slowly with stirring 155 ml. of 1M borane in tetrahydrofuran over a period of 15 minutes. The reaction mixture is then stirred at room temperature for one hour and then heated under reflux with stirring for 5 hours. The mixture is stirred at room temperature for 48 hours. The mixture is stirred and cooled in an ice bath while 45 ml. of 6N hydrochloric acid is added dropwise. The tetrahydrofuran is distilled off on a steam bath and the acidic residue is treated portionwise, with swirling in ice with 35 g. of sodium hydroxide pellets. The reaction mixture is extracted with benzene. The benzene extracts are concentrated, and the residue is repeatedly triturated with ether and filtered. The ether filtrate produces red crystals which are collected, washed with ether and dried. This solid is heated in 60 ml. of benzene to solution, filtered, and the filtrate is concentrated to 30 ml. and cooled. The solid is collected, washed with benzene and hexane and dried giving the desired product, mp. 184°-186° C.

Workup

  1. temperaturewith cooling in an ice bath
  2. additionTo this is added slowly
  3. stirringThe reaction mixture is then stirred at room temperature for one hour
  4. temperatureheated
  5. temperatureunder reflux
  6. stirringwith stirring for 5 hours
  7. stirringThe mixture is stirred at room temperature for 48 hours
  8. stirringThe mixture is stirred
  9. temperaturecooled in an ice bath while 45 ml
  10. distillationThe tetrahydrofuran is distilled off on a steam bath
  11. additionthe acidic residue is treated portionwise
  12. extractionThe reaction mixture is extracted with benzene
  13. concentrationThe benzene extracts are concentrated
  14. customthe residue is repeatedly triturated with ether
  15. filtrationfiltered
  16. customThe ether filtrate produces red crystals which
  17. customare collected
  18. washwashed with ether
  19. customdried
  20. temperatureThis solid is heated in 60 ml
  21. filtrationof benzene to solution, filtered
  22. concentrationthe filtrate is concentrated to 30 ml
  23. temperatureand cooled
  24. customThe solid is collected
  25. washwashed with benzene and hexane
  26. customdried

Sources & evidence

ORD record
ord-af877491b91e4b86b0f786a854fbc983
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

Loading…