Iodine → HCID 10383744, compound

HRID 1755631Notes

Reaction equation

HRID 1755631 reaction equation
FC(F)(F)C(O[I:6](OC(=O)C(F)(F)F)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.[C:22]([N:26]1[C:32](=[O:33])C2C=CC=CC=2[NH:29][C:28](=[O:38])[CH2:27]1)([CH3:25])([CH3:24])[CH3:23].II>C(Cl)Cl.C(OCC)(=O)C>[C:22]([N:26]1[C:32](=[O:33])[C:11]2[CH:12]=[C:7]([I:6])[CH:8]=[CH:9][C:10]=2[NH:29][C:28](=[O:38])[CH2:27]1)([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 807IodineHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 100826661H-1,4-Benzodiazepine-2,5-dione, 4-(1,1-dimethylethyl)-3,4-dihydro-

Product 1

HCID 10383744HCID 10383744, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Bis(trifluoroacetoxy)phenyl iodine (2.05 g, 4.7 mmol) is added to a solution of 4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (1.0 g, 4.3 mmol) and iodine (1.1 g, 4.3 mmol) in methylene chloride. The reaction mixture is stirred overnight at room temperature, diluted with ethyl acetate, washed sequentially with saturated sodium hydrogen carbonate solution, 1N sodium thiosulfate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Chromatography of the residue using silica gel and 20% to 25% ethyl acetate in hexanes solutions gives the title product as a beige solid (0.9 g, mp 230°-232° C.).

Workup

  1. washwashed sequentially with saturated sodium hydrogen carbonate solution, 1N sodium thiosulfate solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue

Sources & evidence

ORD record
ord-bb388ec8658e47fba887d040cd06dcc2
Source dataset
uspto-grants-1995_08
Patent number
US05438035

Reaction notes

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