Potassium Cyanide → methyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate

HRID 67429Notes

Reaction equation

HRID 67429 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[S:10][CH:11]=[CH:12][C:6]=2[N:5]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19]C)=[O:17])=[C:4]2[CH2:3]1.[C-]#N.[K+]>CO>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[S:10][CH:11]=[CH:12][C:6]=2[N:5]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 22914412HCID 22914412, compound

Product 1

HCID 20515348methyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 430 mg (1.5 mmol) of ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]-diazepine-3-carboxylate and 99 mg (1.5 mmol) of potassium cyanide in 15 ml of absolute methanol is heated under reflux for 3 hours while stirring. After evaporation in vacuo, the residue is treated with ca 20 ml of ice/water and extracted three times with ca 30 ml of chloroform each time. The combined chloroform phases are washed twice with ca 20 ml of water each time, dried over magnesium sulphate and evaporated. After washing with boiling ethyl acetate, there is obtained methyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate of melting point 244°-245° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. customAfter evaporation in vacuo
  4. additionthe residue is treated with ca 20 ml of ice/water
  5. extractionextracted three times with ca 30 ml of chloroform each time
  6. washThe combined chloroform phases are washed twice with ca 20 ml of water each time
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. washAfter washing with boiling ethyl acetate

Sources & evidence

ORD record
ord-25d9fc92d77d4692b314017355f6af76
Source dataset
uspto-grants-1982_08
Patent number
US04346032

Reaction notes

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