Pyridine → N-(2-chloro-phenyl)-3-methyl-1,2,4-oxadiazol-5-yl-acetamide

HRID 971708Notes

Reaction equation

HRID 971708 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10].[CH3:15][C:16]1[N:20]=[C:19]([CH2:21][C:22](O)=[O:23])[O:18][N:17]=1>O1CCOCC1.C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][C:22](=[O:23])[CH2:21][C:19]1[O:18][N:17]=[C:16]([CH3:15])[N:20]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 72402-ChloroanilineHCID 213130182-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acid

Product 1

HCID 21312973N-(2-chloro-phenyl)-3-methyl-1,2,4-oxadiazol-5-yl-acetamideYield 77%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

Using the procedure of Example 20, 1.65 ml of dry pyridine and 1.33 ml of 2-chloro-aniline were added successively to a solution of 2.0 g of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid in a mixture of 13 ml of dioxane and 13 ml of toluene and the precipitation of a viscous oil was observed. The reaction mixture was stirred for 90 minutes at room temperature and then was evaporated to dryness. The residue was thoroughly stirred with 10 ml of iced water, whereupon dichloromethane was added. The pH of the resulting, clear two-layer system was 0.8 and the pH was raised to 3.0 and the layers separated. The water layer was extracted 4 times with 25 ml volumes of dichloromethane and the 5 extracts were combined, washed once with a small volume of iced water, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was crystallized from carbon tetrachloride to obtain 2.7 g (77% yield) of pure N-(2-chloro-phenyl)-3-methyl-1,2,4-oxadiazol-5-yl-acetamide with a m.p. of 118.5°-119.5° C.

Workup

  1. customthe precipitation of a viscous oil
  2. customwas evaporated to dryness
  3. stirringThe residue was thoroughly stirred with 10 ml of iced water, whereupon dichloromethane
  4. additionwas added
  5. temperaturethe pH was raised to 3.0
  6. customthe layers separated
  7. extractionThe water layer was extracted 4 times with 25 ml volumes of dichloromethane
  8. washwashed once with a small volume of iced water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was crystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-28dfe0de3b5a4257942035c742e120b3
Source dataset
uspto-grants-1979_07
Patent number
US04160829

Reaction notes

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