Potassium Iodide → 4,9-Dihydro-9-phenethyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1863187Notes

Reaction equation

HRID 1863187 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.[H-].[Na+].[CH2:18](Br)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[I-].[K+]>CN(C)C=O>[CH2:18]([N:8]1[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[NH:5][C:4]2=[CH:3][S:2][CH:1]=[C:10]2[C:9]1=[O:11])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 203922654,9-Dihydro-9-phenethyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 17.28 g. of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of dimethylformamide is added 4.2 g. of 50% sodium hydride in mineral oil. The mixture is stirred for one hour and 16.0 g. of phenethyl bromide and 20 mg. of potassium iodide are added. The mixture is stirred for 48 hours. The solution is evaporated. The residual gum is washed with water and hexane, dissolved in methylene chloride, washed with water, dried over magnesium sulfate and filtered through magnesol. The crystals which form in the filtrate are removed by filtration. This filtrate is evaporated in vacuo giving the desired product as dark brown crystals.

Workup

  1. stirringThe mixture is stirred for 48 hours
  2. customThe solution is evaporated
  3. washThe residual gum is washed with water and hexane
  4. dissolutiondissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered through magnesol
  8. customThe crystals which form in the filtrate
  9. customare removed by filtration
  10. customThis filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-1160cc3d332e476a916e5b7f67887aab
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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