Iodine → HCID 70394533, compound

HRID 1607025Notes

Reaction equation

HRID 1607025 reaction equation
[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[CH:10][S:11](=[O:12])[C:6]=2[N:5]2[CH:13]=[N:14][CH:15]=[C:4]2[CH2:3]1.[I:16]I.C(=O)([O-])O.[Na+]>CN(C)C=O>[I:16][C:15]1[N:14]=[CH:13][N:5]2[C:6]3[S:11](=[O:12])[CH:10]=[CH:9][C:7]=3[CH2:8][N:2]([CH3:1])[CH2:3][C:4]=12

Participants

5

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 70394981HCID 70394981, compound

Product 1

HCID 70394533HCID 70394533, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22 g of 5,6-dihydro-5-methyl-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepine-one was dissolved in 330 ml of dimethylformamide and treated with 50.6 g of iodine. The mixture was stirred at room temperature for 24 hours and then at 30° for 18 hours. It was then poured into 9 l of saturated aqueous sodium hydrogen carbonate solution. This solution was extracted four times with trichloromethane. The trichloromethane solutions were washed in succession with aqueous sodium thiosulphate solution and with aqueous sodium chloride solution, then dried over sodium sulphate and evaporated in a vacuum. The residue was chromatographed through 2.5 kg of silica gel. An impurity was first eluted with trichloromethane. The main product was then eluted with trichloromethane/ethanol mixtures 199:1 and 99:1. These eluates are evaporated in a vacuum and the residue was crystallized several times from ethyl acetate/diisopropyl ether and then from ethyl acetate. There was obtained 5,6-dihydro-7-iodo-5-methyl-4H-imidazo[1,5-a]thieno[3,2-f][ 1,4]diazepine-one of melting point 175°-177°.

Workup

  1. waitat 30° for 18 hours
  2. extractionThis solution was extracted four times with trichloromethane
  3. washThe trichloromethane solutions were washed in succession with aqueous sodium thiosulphate solution and with aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated in a vacuum
  6. customThe residue was chromatographed through 2.5 kg of silica gel
  7. washAn impurity was first eluted with trichloromethane
  8. washThe main product was then eluted with trichloromethane/ethanol
  9. customThese eluates are evaporated in a vacuum
  10. customthe residue was crystallized several times from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-51f6ce2dff18443e9a61c23007c9c3ad
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

Loading…