Tetrahydrofuran → HCID 20392229, compound

HRID 1863180Notes

Reaction equation

HRID 1863180 reaction equation
[CH3:1][C:2](=[CH2:19])[CH2:3][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.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:19][C:2](=[CH2:1])[CH2:3][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

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 20392225HCID 20392225, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20392229HCID 20392229, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 4.9 g. portion of 4,9-dihydro-9-(2-methylallyl)-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of dried tetrahydrofuran is added with stirring and ice bath cooling, under nitrogen, to 2.9 g. of lithium aluminum hydride in 100 ml. of dried tetrahydrofuran. The mixture is refluxed overnight and then decomposed with stirring and cooling under nitrogen by the successive addition of 3 ml. of water, 3 ml. of 15% sodium hydroxide and 9 ml. of water. The complex is filtered and washed with ether. The combined filtrate and washing is dried over sodium sulfate, filtered and evaporated to a residue on a steam bath. The residue is recrystallized from hexane giving the desired product, mp. 83°-84° C.

Workup

  1. temperatureice bath cooling, under nitrogen, to 2.9 g
  2. temperatureThe mixture is refluxed overnight
  3. stirringwith stirring
  4. temperaturecooling under nitrogen by the successive addition of 3 ml
  5. filtrationThe complex is filtered
  6. washwashed with ether
  7. washThe combined filtrate and washing
  8. dry with materialis dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to a residue on a steam bath
  11. customThe residue is recrystallized from hexane giving the desired product, mp. 83°-84° C.

Sources & evidence

ORD record
ord-f133420012fa4585bdae8d022354133b
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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