Methyl iodide → HCID 19917712, compound

HRID 1755634Notes

Reaction equation

HRID 1755634 reaction equation
CI.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][N:10]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:9](=[O:19])[C:8]=2[CH:20]=1.[C:21](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O1CCCC1>[C:15]([N:10]1[C:9](=[O:19])[C:8]2[CH:20]=[C:4]([Cl:3])[CH:5]=[CH:6][C:7]=2[N:13]=[C:12]([O:14][CH3:21])[CH2:11]1)([CH3:17])([CH3:16])[CH3:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1781044-tert-Butyl-7-chloro-1,3-dihydro-1,4-benzodiazepine-2,5-dione

Product 1

HCID 19917712HCID 19917712, compoundYield 118.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl iodide (233 μL, 3.7 mmol) is added to a mixture of 7-chloro-4-tert-butyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (0.5 g, 1.9 mmol) and potassium carbonate (1.04 g, 7.5 mmol) in tetrahydrofuran. The reaction mixture is stirred at room temperature for 16 hours, heated at reflux for 90 hours, filtered through diatomaceous earth and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and 33% to 50% ethyl acetate in hexanes solutions gives the title product as a clear oil (0.63 g) which is identified by 1HNMR spectral analysis.

Workup

  1. temperatureheated
  2. temperatureat reflux for 90 hours
  3. filtrationfiltered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-b8300315a37f4eb684b4f7db31e9ce65
Source dataset
uspto-grants-1995_08
Patent number
US05438035

Reaction notes

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