Propargyl bromide → HCID 14278843, compound

HRID 1905336Notes

Reaction equation

HRID 1905336 reaction equation
[C:1]([C:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([OH:17])[C:14]([Cl:18])=[CH:13][C:12]=2[F:19])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][C:22]#[CH:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[C:15]([O:17][CH2:23][C:22]#[CH:21])[C:14]([Cl:18])=[CH:13][C:12]=2[F:19])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 14278842HCID 14278842, compound

Product 1

HCID 14278843HCID 14278843, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reacted at 80° C. for 6 hours with stirring were 1.2 g of 5-t-butyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,3,4-oxadiazol-2-one, 0.76 g of 3-bromopropyne, 40 ml of acetonitrile, and 0.3 g of potassium carbonate. After cooling, the reaction product was filtered and the filtrate was subjected to vacuum distillation to remove the solvent. To the residue was added 30 ml of methylene chloride, and the solution was washed with a 5% aqueous solution of sodium hydroxide and then with water. Upon removal of the solvent by distillation, 1.31 g of 5-t-butyl-3-(4-chloro-2-fluoro-5-propargyloxyphenyl)-1,3,4-oxadiazol-2-one was obtained. Upon recrystallization from n-hexane, a compound having a melting point of 72°-73° C. was obtained.

Workup

  1. customReacted at 80° C. for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction product was filtered
  4. distillationthe filtrate was subjected to vacuum distillation
  5. customto remove the solvent
  6. additionTo the residue was added 30 ml of methylene chloride
  7. washthe solution was washed with a 5% aqueous solution of sodium hydroxide
  8. customUpon removal of the solvent
  9. distillationby distillation

Sources & evidence

ORD record
ord-99b05d4dcfc44093989241f1e8a7a938
Source dataset
uspto-grants-1989_06
Patent number
US04842640

Reaction notes

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