Iodine → 8-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1493129Notes

Reaction equation

HRID 1493129 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][CH:14]=[C:10]3[CH2:9][N:8]([CH3:15])[C:7](=[O:16])[C:6]=2[CH:17]=1.[I:18]I.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([I:18])=[C:10]3[CH2:9][N:8]([CH3:15])[C:7](=[O:16])[C:6]=2[CH:17]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 24477Sodium ThiosulfateHCID 229145898-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198306858-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.31 g (10 mmol) of 8-fluoro-4,5-dihydro-5-methyl-6H -imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at 95° for 1.5 hours with 8.88 g (35 mmol) of iodine in 25 ml of N,N-dimethylformamide. The reaction mixture was then poured into 300 ml of water, decolorized with sodium thiosulfate solution and extracted four times with methylene chloride. The organic extracts were washed three times with water, dried over magnesium sulfate and evaporated. After recrystallization of the residue from ethyl acetate there was obtained 8-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 187-188°.

Workup

  1. extractionextracted four times with methylene chloride
  2. washThe organic extracts were washed three times with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customAfter recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-4c9be8f8b4b7492b82d75f8f01932718
Source dataset
uspto-grants-1991_06
Patent number
US05021411

Reaction notes

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