N-Methylbenzylamine → 5-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazole

HRID 247112

Reaction equation

HRID 247112 reaction equation
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10]Cl)[N:6]=1)[C:2]([CH3:4])=[O:3].[CH3:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C(Cl)(Cl)Cl.CO>CN(C=O)C>[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][N:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:12])[N:6]=1)[C:2]([CH3:4])=[O:3]

Participants

6

Reactant 4

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazoleHCID 21584188Chloroform methanol

Product 1

HCID 201612565-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazoleYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 800 mg of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 720 mg of N-methylbenzylamine and 1.0 g of triethylamine in 5 ml of DMF was stirred at room temperature for 8 hours. The reaction mixture was then poured into ice-water and the resultant mixture was extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo to yield a brown oil. Chromatography on silica gel using chloroform-methanol (20:1, v/v) as eluent afforded 780 mg of 5-acetonyl-3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazole as a colorless oil, IR νmaxneat cm-1 : 1730, 1635, 1580, 1545, 1450, 1360.

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield a brown oil

Sources & evidence

ORD record
ord-303c850ae3a546e8b488f5e8da837353
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Linked notes

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