Iodine → HCID 19830655, compound

HRID 1493126Notes

Reaction equation

HRID 1493126 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:15]=[N:16][CH:17]=[C:4]2[CH2:3]1.[I:18]I.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(Cl)Cl.O>[I:18][C:17]1[N:16]=[CH:15][N:5]2[C:6]3[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:7]=3[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][C:4]=12

Participants

8

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 19830657HCID 19830657, compound

Product 1

HCID 19830655HCID 19830655, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

15.85 g (69.7 mmol) of 4,5-dihydro-5,7-dimethyl-6H -imidazo[1,5-a][1,4]benzodiazepin-6-one were heated to 95° for 2.5 hours with 67 g (264 mmol) of iodine in 100 ml of N,N-dimethylformamide. The reaction mixture was then poured into 450 ml of water, treated with methylene chloride, decolorized with sodium thiosulfate and neutralized with sodium bicarbonate. The aqueous phase was separated and extracted six times with methylene chloride. The combined organic phases were washed three times with water, dried over magnesium sulfate and evaporated. By chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate and hexane, there was obtained 4,5-dihydro-3-iodo-5,7-dimethyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 106-108°.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted six times with methylene chloride
  3. washThe combined organic phases were washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. washBy chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-d62a5198ba0a4f62b176b7fcf630658c
Source dataset
uspto-grants-1991_06
Patent number
US05021411

Reaction notes

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