Hydrochloric Acid → HCID 20392273, compound

HRID 1863185Notes

Reaction equation

HRID 1863185 reaction equation
B.[C:2]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH3:16])[C:8](=O)[C:7]2=[CH:18][S:19][CH:20]=[C:6]12)(=O)[CH3:3].Cl>O1CCCC1>[CH2:2]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH3:16])[CH2:8][C:7]2=[CH:18][S:19][CH:20]=[C:6]12)[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 20392230HCID 20392230, compound

Product 1

HCID 20392273HCID 20392273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 150 ml. portion of 1M-borane in tetrahydrofuran is added with stirring and cooling to a solution of 5.1 g. of 4-acetyl-4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]-benzodiazepin-10-one in 200 ml. of tetrahydrofuran. The reaction mixture is heated under reflux for 20 hours, cooled in an ice bath and 52 ml. of 6N hydrochloric acid is added dropwise with stirring. The tetrahydrofuran is removed by distillation. A 40 g. portion of sodium hydroxide pellets is carefully added in the cold with stirring followed by 25 ml. of water. The mixture is extracted with three 150 ml. portions of benzene. The benzene extracts are combined, washed with water, dried over sodium sulfate, filtered and concentrated to dryness. The residue is extracted three times with boiling hexane. The combined hexane extracts are cooled and the solid is collected, washed with hexane and ether and dried. A second crop is recovered from the hexane filtrate and combined with the first crop. The solid is dissolved in 25 ml. of methylene chloride, filtered and the solvent is evaporated almost to dryness. A 50 ml. portion of hexane is added. The solid is collected, washed with hexane and dried, giving the desired product as white crystals, mp. 135°-137° C.

Workup

  1. temperaturecooling to a solution of 5.1 g
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 20 hours
  4. temperaturecooled in an ice bath
  5. stirringwith stirring
  6. customThe tetrahydrofuran is removed by distillation
  7. additionportion of sodium hydroxide pellets is carefully added in the cold
  8. stirringwith stirring
  9. extractionThe mixture is extracted with three 150 ml
  10. washwashed with water
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness
  14. extractionThe residue is extracted three times with boiling hexane
  15. temperatureThe combined hexane extracts are cooled
  16. customthe solid is collected
  17. washwashed with hexane and ether
  18. customdried
  19. customA second crop is recovered from the hexane filtrate
  20. dissolutionThe solid is dissolved in 25 ml
  21. filtrationof methylene chloride, filtered
  22. customthe solvent is evaporated almost to dryness
  23. additionportion of hexane is added
  24. customThe solid is collected
  25. washwashed with hexane
  26. customdried

Sources & evidence

ORD record
ord-43acf06cbdca47999268e14181bd3421
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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