HCID 13690971, compound → HCID 13690972, compound

HRID 2290776Notes

Reaction equation

HRID 2290776 reaction equation
Cl[CH2:2][CH2:3][C:4]1[N:8]=[C:7]([CH:9]([CH3:23])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([F:22])[CH:11]=2)[O:6][N:5]=1.[C:24]([O-:27])(=[S:26])[CH3:25].[K+]>CN(C=O)C>[C:24]([S:26][CH2:2][CH2:3][C:4]1[N:8]=[C:7]([CH:9]([CH3:23])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([F:22])[CH:11]=2)[O:6][N:5]=1)(=[O:27])[CH3:25]

Participants

4

Reactant 2

HCID 13690971HCID 13690971, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 13690972HCID 13690972, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.44 g of 3-(2-chloroethyl)-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole in 40 ml of DMF was added 1.69 g of potassium thioacetate. After stirring at room temperature overnight, the reaction mixture was poured into ice-water. The resultant mixture was extracted with benzene and the organic phase was washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel using benzene to yield 2.62 g of 3-(2-acetylthioethyl)-5-(3-fluoro-4-phenyl-α-methylbenzyl)-1,2,4-oxadiazole as a light brown oil. It was crystallized from diisopropyl ether to give colorless needles, m.p. 56°-57° C.

Workup

  1. extractionThe resultant mixture was extracted with benzene
  2. washthe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-980effae0380436ea97e2a0965f67dbd
Source dataset
uspto-grants-1986_10
Patent number
US04618617

Reaction notes

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