Sodium Cyanide → 3-Cyanomethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

HRID 2290770Notes

Reaction equation

HRID 2290770 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1.[C-:23]#[N:24].[Na+]>CS(C)=O>[C:23]([CH2:2][C:3]1[N:7]=[C:6]([CH:8]([CH3:22])[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[O:5][N:4]=1)#[N:24]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 136909413-Chloromethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazole

Product 1

HCID 136909683-Cyanomethyl-5-(3-fluoro-4-phenyl-alpha-methylbenzyl)-1,2,4-oxadiazoleYield 64.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3.82 g of 3-chloromethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole in 50 ml of dimethyl sulfoxide (DMSO) was added 0.75 g of sodium cyanide. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice-water. The resultant mixture was extracted with benzene and the extracts were washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed over silica gel using benzene to yield 2.4 g of 3-cyanomethyl-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole. It was recrystallized from ethyl acetate-diisopropyl ether to give colorless plates, m.p. 111°-112° C.

Workup

  1. extractionThe resultant mixture was extracted with benzene
  2. washthe extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-f9d40fd4cee945d3b940facc7be6ee49
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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