Iodine → HCID 19851566, compound

HRID 1607018Notes

Reaction equation

HRID 1607018 reaction equation
[Cl: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][C:3]=1[F:18].[I:19]I>CN(C)C=O>[Cl: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:19])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:18]

Participants

4

Reactant 2

HCID 807IodineHCID 19851550HCID 19851550, compound

Product 1

HCID 19851566HCID 19851566, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.08 g (22.8 mmol) of 7-chloro-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was stirred at 100° for 4 hours with 20 g (79.5 mmol) of iodine in 50 ml of N,N-dimethylformamide. The reaction mixture was evaporated, the residue was taken up in methylene chloride and water, decolorized with sodium thiosulphate and neutralized with sodium bicarbonate. The aqueous phase was separated and extracted four times with methylene chloride. The combined organic phases were dried over magnesium sulphate, evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate/hexane (1:1). There was obtained 7-chloro-8-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 218°-219°.

Workup

  1. customThe reaction mixture was evaporated
  2. customThe aqueous phase was separated
  3. extractionextracted four times with methylene chloride
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. customevaporated
  6. customthe residue was chromatographed on silica gel
  7. washwhile eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-646da50038b24473a13e7bf2baeb2753
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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