Methylamine → N-methyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)benzamide

HRID 328116Notes

Reaction equation

HRID 328116 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]=1.[CH3:22][NH2:23]>CCOCC.O>[C:15]1([C:12]2[N:11]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([NH:23][CH3:22])=[O:2])[O:14][N:13]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 54140169Methyl 2-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoate

Product 1

HCID 3604966N-methyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 6.16 g. (0.022 mole) o-(3-phenyl-1,2,4-oxadiazol-5-yl)-benzoic acid methyl ester in 150 milliliters ether is treated with 150 milliliters 40 percent methyl amine in water. The resulting two-phase system is stirred vigorously for 19 hours. The ether is evaporated, and the resulting mixture extracted with methylene chloride. The organic phase is washed with water and then brine, dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The resulting solid is triturated with ether and filtered to give o-(3-phenyl-1,2,4-oxadiazol-5-yl)-N-methyl benzamide, m.p. 145°-146° C.

Workup

  1. customThe ether is evaporated
  2. extractionthe resulting mixture extracted with methylene chloride
  3. washThe organic phase is washed with water
  4. dry with materialbrine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting solid is triturated with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-22e2f96bee9647b49d3d2a48a2afc540
Source dataset
uspto-grants-1977_04
Patent number
US04016170

Reaction notes

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