Iodine → HCID 19830655, compound

HRID 1607020Notes

Reaction equation

HRID 1607020 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 was 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 thiosulphate 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 sulphate 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 sulphate
  5. customevaporated
  6. washBy chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2f3f36c7ba4b4568be71c2d41da89d84
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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