Tetrahydrofuran → HCID 20392261, compound

HRID 1863174Notes

Reaction equation

HRID 1863174 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[Cl:12][C:13]1[C:28]([Cl:29])=[CH:27][C:16]2[N:17]([CH3:26])[C:18](=O)[C:19]3[C:20](=[CH:22][S:23][CH:24]=3)[NH:21][C:15]=2[CH:14]=1.[OH-].[Na+]>O>[Cl:12][C:13]1[C:28]([Cl:29])=[CH:27][C:16]2[N:17]([CH3:26])[CH2:18][C:19]3[C:20](=[CH:22][S:23][CH:24]=3)[NH:21][C:15]=2[CH:14]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 20392233HCID 20392233, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20392261HCID 20392261, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of 4 g. of lithium aluminum hydride in 150 ml. of tetrahydrofuran stirred under nitrogen, is added a solution of 10 g. of 6,7-dichloro-4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 350 ml. of tetrahydrofuran. The mixture is stirred under reflux for 31/2 hours and then allowed to stand overnight. The mixture is cooled in an ice bath and treated, under nitrogen with stirring, with 4 ml. of water, 4 ml. of 15% sodium hydroxide and 12 ml. of water. The complex is filtered and washed with ether. The combined filtrate and washing is dried over sodium sulfate, filtered and concentrated to a residue. This residue is dissolved in a mixture of 10 ml. of 30% methylene chloride in hexane and 10 ml. of methylene chloride and chromatographed on an alumina column as described in Example 20. Those fractions which contain the desired product as determined by thin layer chromatography are combined and concentrated to give a blue-green crystalline solid. The crystalline product is heated to the boil in 200 ml. of hexane, and filtered. The filtrate is cooled and an standing produces a solid which is collected, washed with hexane and dried giving the desired product, mp. 92°-93° C.

Workup

  1. additionTo a suspension of 4 g
  2. additionis added a solution of 10 g
  3. temperatureunder reflux for 31/2 hours
  4. temperatureThe mixture is cooled in an ice bath
  5. additiontreated, under nitrogen
  6. stirringwith stirring, with 4 ml
  7. filtrationThe complex is filtered
  8. washwashed with ether
  9. washThe combined filtrate and washing
  10. dry with materialis dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated to a residue
  13. dissolutionThis residue is dissolved in a mixture of 10 ml
  14. customof methylene chloride and chromatographed on an alumina column
  15. concentrationconcentrated
  16. customto give a blue-green crystalline solid
  17. temperatureThe crystalline product is heated to the boil in 200 ml
  18. filtrationof hexane, and filtered
  19. temperatureThe filtrate is cooled
  20. customan standing produces a solid which
  21. customis collected
  22. washwashed with hexane
  23. customdried

Sources & evidence

ORD record
ord-1eb4d072049848218abdd3a48301b6b1
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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