Allyl bromide → HCID 178460728, compound

HRID 1065793Notes

Reaction equation

HRID 1065793 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([SH:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15]>C(COC)OC>[C:1]([C:5]1[CH:9]=[C:8]([S:10][CH2:15][CH:14]=[CH2:13])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178441225HCID 178441225, compound

Product 1

HCID 178460728HCID 178460728, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a slurry of 3-t-butylpyrazole-5-thiol (10 g) in dry dimethoxyethane (100 ml) was added portionwise, with stirring, sodium hydride (1.6 g). Stirring at room temperature was continued for a few minutes, and then allyl bromide (7.8 g) was added. The reaction mixture was stirred for 2 hours, filtered, and evaporated. The residue was dissolved in ether and washed with water, and the ether layer separated, dried, and evaporated to give 3-t-butyl-5-(allylthio)pyrazole, as a pale brown oil (11.0 g), 88% yield.

Workup

  1. stirringStirring at room temperature
  2. waitwas continued for a few minutes
  3. stirringThe reaction mixture was stirred for 2 hours
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in ether
  7. washwashed with water
  8. customthe ether layer separated
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-625453a54a47419cb84bf051042b3648
Source dataset
uspto-grants-1982_05
Patent number
US04331678

Reaction notes

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