Ethyl Acetate → HCID 10403166, compound

HRID 1755630Notes

Reaction equation

HRID 1755630 reaction equation
[Br:1]Br.[C:3]([N:7]1[C:13](=[O:14])[C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[NH:10][C:9](=[O:19])[CH2:8]1)([CH3:6])([CH3:5])[CH3:4].C([O-])(=O)C.[Na+].C(OCC)(=O)C>C(O)(=O)C>[Br:1][C:16]1[CH:17]=[CH:18][C:11]2[NH:10][C:9](=[O:19])[CH2:8][N:7]([C:3]([CH3:6])([CH3:4])[CH3:5])[C:13](=[O:14])[C:12]=2[CH:15]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 517045Sodium AcetateHCID 100826661H-1,4-Benzodiazepine-2,5-dione, 4-(1,1-dimethylethyl)-3,4-dihydro-

Product 1

HCID 10403166HCID 10403166, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (1.72 g, 10.8 mmol) is added to a mixture of 4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (1.0 g, 4.3 mmol) and sodium acetate (0.39 g, 4.8 mmol) in acetic acid. The reaction mixture is stirred at room temperature for 29 hours, concentrated in vacuo, diluted with ethyl acetate, washed sequentially with 0.1N sodium hydroxide solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue. Chromatography of the residue using silica gel and 20% to 25% ethyl acetate in hexanes solutions gives the title product as a white solid (0.86 g, mp 205°-208° C.).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed sequentially with 0.1N sodium hydroxide solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-dab398a0f9f7430081f72a7e6c45e221
Source dataset
uspto-grants-1995_08
Patent number
US05438035

Reaction notes

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