Acetone → HCID 18327516, compound

HRID 636670Notes

Reaction equation

HRID 636670 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[S:8][N:7]=[N:6][C:5]=1[CH3:9].[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]([CH3:23])=O>>[CH2:10]([N:2]([CH2:3][C:4]1[S:8][N:7]=[N:6][C:5]=1[CH3:9])[CH2:23][CH:21]=[CH2:20])[CH:11]=[CH2:12]

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 18327524HCID 18327524, compound

Product 1

HCID 18327516HCID 18327516, compoundYield 67%

Procedure

To 15 ml of acetone were added 0.50 g (3.0 mmol) of 5-aminomethyl-4-methyl-1,2,3-thiadiazole hydrochloride, 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-c53d5493ae2e4d4498e5d29cbf5be73c
Source dataset
uspto-grants-2001_02
Patent number
US06194444B1

Reaction notes

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