Tetrahydrofuran → HCID 20392266, compound

HRID 1863171Notes

Reaction equation

HRID 1863171 reaction equation
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]2=[CH:15][S:16][CH:17]=[C:6]2[C:5]1=O)[CH2:2][CH3:3].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]2=[CH:15][S:16][CH:17]=[C:6]2[CH2:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 20392242HCID 20392242, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20392266HCID 20392266, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 5 g. portion of 4,9-dihydro-9-propyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of dried tetrahydrofuran is added dropwise with stirring under nitrogen to a suspension of 3.1 g. of lithium aluminum hydride in 100 ml. of tetrahydrofuran. The reaction mixture is stirred for 18 hours under reflux, then cooled in an ice bath and treated under nitrogen, with stirring, with 3 ml. of water, 3 ml. of 15% sodium hydroxide and finally with 9 ml. of water. The complex is filtered and washed thoroughly with ether. The combined filtrate and washings are dried over sodium sulfate and filtered. The filtrate is concentrated to a dark blue oil. A 50 ml. portion of hexane:ether (10:1) is added and the mixture is stored in a chill room overnight. The solid is filtered, washed with hexane and dried. A second crop is obtained from the filtrate and is washed with hexane and dried. The two crops are combined, heated to solution in 100 ml. of hexane, filtered and cooled giving blue crystals which are collected, washed with hexane and dried, mp. 78°-79° C.

Workup

  1. stirringThe reaction mixture is stirred for 18 hours
  2. temperatureunder reflux
  3. temperaturecooled in an ice bath
  4. additiontreated under nitrogen
  5. stirringwith stirring, with 3 ml
  6. filtrationThe complex is filtered
  7. washwashed thoroughly with ether
  8. dry with materialThe combined filtrate and washings are dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated to a dark blue oil
  11. additionportion of hexane:ether (10:1) is added
  12. customis stored in a chill room overnight
  13. filtrationThe solid is filtered
  14. washwashed with hexane
  15. customdried
  16. customA second crop is obtained from the filtrate
  17. washis washed with hexane
  18. customdried
  19. temperatureheated to solution in 100 ml
  20. filtrationof hexane, filtered
  21. temperaturecooled
  22. customgiving blue crystals which
  23. customare collected
  24. washwashed with hexane
  25. customdried

Sources & evidence

ORD record
ord-368a9003d839432c98e77c4ccbd8a587
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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