Benzyl Bromide → HCID 18327527, compound

HRID 636664Notes

Reaction equation

HRID 636664 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH2:7][OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(C)=O>[CH3:1][C:2]1[N:3]=[N:4][S:5][C:6]=1[CH2:7][O:8][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18411623(4-Methyl-1,2,3-thiadiazol-5-yl)methanol

Product 1

HCID 18327527HCID 18327527, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 10 ml of acetone was dissolved 0.40 g (3.1 mmol) of 4-methyl-1,2,3-thiadiazol-5-ylmethanol. After adding 1.6 g (12 mmol) of potassium carbonate and 0.80 g (4.5 mmol) of benzyl bromide, the resulting mixture was stirred for 10 hours with heating under reflux. After the reaction was completed, the insoluble matter was filtered off, the solvent was distilled off from the filtrate under reduced pressure, and the residue was purified by silica gel column chromatography using 3:1 mixture of n-hexane and ethyl acetate. Thus, 0.65 g of the objective compound was obtained.

Workup

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

Sources & evidence

ORD record
ord-93f64fd4f2f14467bbc56368ae89ddf4
Source dataset
uspto-grants-2001_02
Patent number
US06194444B1

Reaction notes

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