Sodium Chloride → 3-(Chloromethyl)-5-ethyl-1,2,4-oxadiazole

HRID 2261312Notes

Reaction equation

HRID 2261312 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][OH:6])=[NH:4].[C:7](Cl)(=O)[CH2:8][CH3:9].C(N(CC)CC)C.[Cl-].[Na+]>CN(C)C=O>[Cl:1][CH2:2][C:3]1[N:4]=[C:7]([CH2:8][CH3:9])[O:6][N:5]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178511097HCID 178511097, compound

Product 1

HCID 199286713-(Chloromethyl)-5-ethyl-1,2,4-oxadiazoleYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2.0 g of 2-chloro-N-hydroxyacetoamidine and 1.80 g of propionyl chloride were dissolved in 50 ml of N,N-dimethylformamide, and 2.05 g of triethylamine was added dropwise under ice-cooling. The mixture was stirred at 130° C. for 5 hours and then cooled to room temperature. After aqueous saturated sodium chloride was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.62 g of 3-(chloromethyl)-5-ethyl-1,2,4-oxadiazole.

Workup

  1. temperaturecooling
  2. temperaturecooled to room temperature
  3. extractionthe reaction mixture was extracted with methyl-t-butyl ether
  4. washThe organic layer was washed with aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dde39b4b6a6c447886d63565205c1794
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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