Acetone → HCID 18327516, compound

HRID 1250202Notes

Reaction equation

HRID 1250202 reaction equation
[NH2:1][CH2:2][C:3]1[S:7][N:6]=[N:5][C:4]=1[CH3:8].[CH2:9](Br)[CH:10]=[CH2:11].C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]([CH3:22])=O>>[CH2:9]([N:1]([CH2:2][C:3]1[S:7][N:6]=[N:5][C:4]=1[CH3:8])[CH2:22][CH:20]=[CH2:19])[CH:10]=[CH2:11]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 183275251-(4-Methyl-1,2,3-thiadiazol-5-yl)methanamine

Product 1

HCID 18327516HCID 18327516, compoundYield 67%

Procedure

To 15 ml of acetone were added 0.50 g (3.0 mol) of 5-aminomethyl-4-methyl-1,2,3-thiadiazole ydrochloride, 1.10 g (9.0 mmol) of allyl bromide and 2.1 g (15 mmol) of potassium carbonate. The resulting mixture was stirred for 20 hours with heating under reflux. After the reaction was completed, the reaction mixture was filtered to remove the precipitated matter, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 3:1 mixture of n-hexane and ethyl acetate. Thus, 0.42 g of the objective compound was obtained.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. filtrationthe reaction mixture was filtered
  4. customto remove the precipitated matter
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. addition3:1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-8b2aa95c5fcf440f98b26a260ee1e7ef
Source dataset
uspto-grants-2002_01
Patent number
US06337341B1

Reaction notes

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