Iodine → HCID 19830661, compound

HRID 1606976Notes

Reaction equation

HRID 1606976 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 was 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 thiosulphate. The mixture was filtered and the filtrate was 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 thiosulphate
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. washAfter chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from methylene chloride

Sources & evidence

ORD record
ord-25a13e8ec5af442ea26b58fae68874e4
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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