Methyl iodide → 2-(methylthio)-7-chloro-5-phenyl-3H-1,5-benzodiazepin-4-one

HRID 258538Notes

Reaction equation

HRID 258538 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7](=[S:18])[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[OH-].[Na+].[CH3:23]I>CO>[CH3:23][S:18][C:7]1[CH2:8][C:9](=[O:17])[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]2[CH:3]=[C:2]([Cl:1])[CH:20]=[CH:19][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 122643197-chloro-5-phenyl-1H-1,5-benzodiazepin-4-one-2-thione

Product 1

HCID 203293232-(methylthio)-7-chloro-5-phenyl-3H-1,5-benzodiazepin-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 3.03 g of 7-chloro-5-phenyl-1H-1,5-benzodiazepin-4-one-2-thione in a solution of 0.40 g of sodium hydroxide and 15 ml of methanol is added, with stirring a solution of 1.4 g of methyl iodide in 10 ml of methanol. Stirring is continued for 1 hour, the reaction is then evaporated and suspended in methylene chloride (30 ml). The suspension is filtered through a short Florisil column; the column is washed with ethyl acetate and the combined filtrates are evaporated. The residue is triturated with a minimum amount of absolute ethanol and the title compound is filtered off and dried.

Workup

  1. customthe reaction is then evaporated
  2. filtrationThe suspension is filtered through a short Florisil column
  3. washthe column is washed with ethyl acetate
  4. customthe combined filtrates are evaporated
  5. customThe residue is triturated with a minimum amount of absolute ethanol
  6. filtrationthe title compound is filtered off
  7. customdried

Sources & evidence

ORD record
ord-85653a3932234c49b47996d6c6c4842a
Source dataset
uspto-grants-1977_07
Patent number
US04033947

Reaction notes

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