Potassium Iodide → 9-[4-chloro-3-(trifluoromethyl)benzyl]-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1863188Notes

Reaction equation

HRID 1863188 reaction equation
[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5]2.[H-].[Na+].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][C:20]=1[C:27]([F:30])([F:29])[F:28].[I-].[K+]>CN(C)C=O>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:8]2[C:7]3[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=3[NH:5][C:4]3=[CH:3][S:2][CH:1]=[C:10]3[C:9]2=[O:11])=[CH:21][C:20]=1[C:27]([F:28])([F:29])[F:30]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneHCID 130942621-Chloro-4-(chloromethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 203922589-[4-chloro-3-(trifluoromethyl)benzyl]-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.64 g. of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of dimethylformamide is added 2.1 g. of 50% sodium hydride in mineral oil. The mixture is stirred for one hour and 10.0 g. of 4-chloro-3-trifluoromethyl benzyl chloride and 10 mg of potassium iodide are added. The mixture is stirred for a prolonged period and the solvent is removed in vacuo. The residual gum is dissolved in methylene chloride, dried over magnesium sulfate and filtered through magnesol. The filtrate is evaporated to give tan crystals which are recrystallized from ethanol giving the desired product as off-white crystals, mp. 181°-183° C.

Workup

  1. stirringThe mixture is stirred for a prolonged period
  2. customthe solvent is removed in vacuo
  3. dissolutionThe residual gum is dissolved in methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through magnesol
  6. customThe filtrate is evaporated
  7. customto give tan crystals which
  8. customare recrystallized from ethanol giving the desired product as off-white crystals, mp. 181°-183° C.

Sources & evidence

ORD record
ord-4b9804bd98b641c691ff56b341ba740a
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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