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

HRID 261221Notes

Reaction equation

HRID 261221 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 sodium hydroxide and 15 ml of methanol is added, with stirring a solution of 1.39 g of methyl iodide in 5 ml of methanol. Stirring is continued for 1 hour, the reaction is evaporated, diluted with 30 ml methylene chloride and filtered through a short Florisil column. After washing the column with ethyl acetate, the combined filtrates are evaporated to give the title compound.

Workup

  1. customthe reaction is evaporated
  2. additiondiluted with 30 ml methylene chloride
  3. filtrationfiltered through a short Florisil column
  4. washAfter washing the column with ethyl acetate
  5. customthe combined filtrates are evaporated

Sources & evidence

ORD record
ord-23b108c03cfe4df0a6d920a910f678fc
Source dataset
uspto-grants-1979_08
Patent number
US04164580

Reaction notes

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