4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one → HCID 20392256, compound

HRID 1863189Notes

Reaction equation

HRID 1863189 reaction equation
[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5]2>CN(C)C=O>[CH:15]1([N:8]2[C:7]3[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=3[NH:5][C:4]3=[CH:3][S:2][CH:1]=[C:10]3[C:9]2=[O:11])[CH2:14][CH2:13][CH2:12][CH:7]=[CH:6]1

Participants

3

Reactant 1

HCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 20392256HCID 20392256, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 11.8 g. of 4,9-dihydro-10H-thieno [3,4-b][1,5]benzodiazepin-10-one in 175 ml. of dimethylformamide is added 2.8 g. of 50% sodium hydride in mineral oil from which the mineral oil has been removed. The mixture is stirred for two hours and then 11.9 g. of 3-bromocyclohexene is added. The reaction mixture is stirred overnight and poured into ice water. The brown syrup which separates is collected and extracted into methylene chloride. The extracts are washed with water, dried over sodium sulfate, filtered and evaporated to an oil. The oil is triturated in ether-hexane and cooled for 48 hours. The mixture is separated by partition chromatography. Fraction 3 is triturated in hexane, filtered and the solid is dried. The solid is triturated in hexane and chilled producing crystals. The crystals are collected, washed with hexane and dried. These crystals are heated to solution in 12 ml. of ethanol and cooled. A 12 ml. portion of hexane is added and the tan crystals are collected, washed with hexane and dried giving the desired product, mp. 147°-149° C.

Workup

  1. additionTo a mixture of 11.8 g
  2. customof 50% sodium hydride in mineral oil from which the mineral oil has been removed
  3. additionof 3-bromocyclohexene is added
  4. stirringThe reaction mixture is stirred overnight
  5. additionpoured into ice water
  6. customThe brown syrup which separates is collected
  7. extractionextracted into methylene chloride
  8. washThe extracts are washed with water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated to an oil
  12. customThe oil is triturated in ether-hexane
  13. temperaturecooled for 48 hours
  14. customThe mixture is separated
  15. customby partition chromatography
  16. customFraction 3 is triturated in hexane
  17. filtrationfiltered
  18. customthe solid is dried
  19. customThe solid is triturated in hexane
  20. temperaturechilled
  21. customproducing crystals
  22. customThe crystals are collected
  23. washwashed with hexane
  24. customdried
  25. temperatureThese crystals are heated to solution in 12 ml
  26. temperatureof ethanol and cooled
  27. additionportion of hexane is added
  28. customthe tan crystals are collected
  29. washwashed with hexane
  30. customdried

Sources & evidence

ORD record
ord-e8aa154f036746029a1dcb80e163a265
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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