Water → HCID 19917717, compound

HRID 1755635Notes

Reaction equation

HRID 1755635 reaction equation
ClCl.[C:3]([N:7]1[C:13](=[O:14])[C:12]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:11]=2[NH:10][C:9](=[O:20])[CH2:8]1)([CH3:6])([CH3:5])[CH3:4].O.C(Cl)[Cl:23].C(OCC)(=O)C>C(O)(=O)C>[Cl:23][C:18]1[C:11]2[NH:10][C:9](=[O:20])[CH2:8][N:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:13](=[O:14])[C:12]=2[CH:15]=[C:16]([CH3:19])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24526ChlorineHCID 1781061H-1,4-Benzodiazepine-2,5-dione, 4-(1,1-dimethylethyl)-3,4-dihydro-7-methyl-HCID 21226138Dichloromethane ethylacetate

Product 1

HCID 19917717HCID 19917717, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Chlorine gas (100 mL, 4.1 mmol) is added via syringe to a mixture of 4-tert-butyl-3,4-dihydro-7-methyl-1H-1,4-benzodiazepine-2,5-dione (1.0 g, 4.1 mmol) and a few grains of ferric chloride hexahydrate in acetic acid. The reaction mixture is stirred at room temperature overnight, poured into water and extracted with ethyl acetate. The combined organic extracts are washed sequentially with water, dilute sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a foam. Flash column chromatography of the foam using silica gel and a 20:1 methylene chloride/ethyl acetate solution gives the title product as a white solid (0.5 g, mp 151°-152° C.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts are washed sequentially with water, dilute sodium hydrogen carbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a foam

Sources & evidence

ORD record
ord-c5f9393d272d4599984d24d4d4733c7f
Source dataset
uspto-grants-1995_08
Patent number
US05438035

Reaction notes

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