Triethylamine → HCID 20161261, compound

HRID 247116Notes

Reaction equation

HRID 247116 reaction equation
[CH2:1]([N:8]([CH3:13])[C:9]([NH2:12])=[N:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:21]=[C:22]1[O:26][C:24](=O)[CH2:23]1>C1C=CC=CC=1>[CH2:23]([C:24]1[O:11][N:10]=[C:9]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:13])[N:12]=1)[C:22]([CH3:21])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 53901949HCID 53901949, compound

Product 1

HCID 20161261HCID 20161261, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a cooled mixture of 2.8 g of 1-benzyl-1-methylhydroxyguanidine and 1.3 g of triethylamine in 30 ml of benzene was added dropwise 1.3 ml of diketene under nitrogen. The reaction mixture was stirred at room temperature for 2 hours and then concentrated in vacuo. After adding 50 ml of toluene to the residue, the resultant solution was heated under reflux for 4 hours with a water separator. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel using chloroform-methanol (70:1) as eluent to give 1.7 g of 5-acetonyl-3-(N-benzyl-N-methylamino)-1,2,4-oxadiazole as a colorless oil, IR νmaxneat cm-1 : 1725, 1590, 1410, 1355, 1155.

Workup

  1. concentrationconcentrated in vacuo
  2. additionAfter adding 50 ml of toluene to the residue
  3. temperaturethe resultant solution was heated
  4. temperatureunder reflux for 4 hours with a water separator
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-ce51e3f62a594f23b3a50da09d8f3b7b
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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