Iodine → HCID 19830661, compound

HRID 1493131Notes

Reaction equation

HRID 1493131 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:17])[N:9]([CH3:16])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][CH:15]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[I:18]I>CN(C)C=O>[Br:1][C:2]1[C:7]2[C:8](=[O:17])[N:9]([CH3:16])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[I:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 807IodineHCID 19830647HCID 19830647, compound

Product 1

HCID 19830661HCID 19830661, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.80 g (44 mmol) of 7-bromo-4,5-dihydro-5-methyl-6H -imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at 95° for 3.5 hours with 39 g (154 mmol) of iodine in 80 ml of N,N-dimethylformamide. The reaction mixture was evaporated, the residue was taken up in methylene chloride and water and decolorized by the addition of sodium thiosulfate. The mixture was filtered the organic phase was separated, dried over magnesium sulfate and evaporated. After chromatography of the residue on silica gel while eluting with ethyl acetate, and recrystallization from methylene chloride and ethyl acetate there was obtained 7-bromo-4,5-dihydro-3-iodo-5-methyl-6H-imidazo [1,5-a][1,4]benzodiazepin-6-one of melting point 203-204°.

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater and decolorized by the addition of sodium thiosulfate
  3. filtrationThe mixture was filtered the organic phase
  4. customwas separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. washAfter chromatography of the residue on silica gel while eluting with ethyl acetate, and recrystallization from methylene chloride

Sources & evidence

ORD record
ord-c37bdec388b74d258834eb8295597435
Source dataset
uspto-grants-1991_06
Patent number
US05021411

Reaction notes

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