Methyl iodide → 4,5-Dihydro-4-methyl-3-methylthio-1-phenyl-1H-2,4-benzodiazepine

HRID 54966

Reaction equation

HRID 54966 reaction equation
[CH3:1][N:2]1[C:8](=[S:9])[NH:7][CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH2:3]1.[CH3:20]I>C(O)C>[CH3:1][N:2]1[C:8]([S:9][CH3:20])=[N:7][CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 149783071,2,4,5-Tetrahydro-4-methyl-1-phenyl-3H-2,4-benzodiazepin-3-thione

Product 1

HCID 149783084,5-Dihydro-4-methyl-3-methylthio-1-phenyl-1H-2,4-benzodiazepineYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 8 g (30 mmol) of the thione of Example 152 and 2.7 mL (44 mmol) of methyl iodide in 100 mL of ethanol was refluxed two hours, cooled, and the hydriodide of the product filtered off. The salt was partitioned between methylene chloride and aqueous sodium bicarbonate, the organic layer dried over magnesium sulfate, and stripped. The residue was dissolved in ethanol and 2.7 g of methanesulfonic acid was added followed by ether. The resulting precipitate was filtered off and recrystallized from ethanol to yield 5.2 g of product as the methanesulfonate salt, mp 195-196.

Workup

  1. temperaturecooled
  2. filtrationthe hydriodide of the product filtered off
  3. customThe salt was partitioned between methylene chloride and aqueous sodium bicarbonate
  4. dry with materialthe organic layer dried over magnesium sulfate
  5. dissolutionThe residue was dissolved in ethanol
  6. addition2.7 g of methanesulfonic acid was added
  7. filtrationThe resulting precipitate was filtered off
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b2b78206a01149dea27cda774b5148b9
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Linked notes

Loading…