Allyl bromide → HCID 21287136, compound

HRID 1758537Notes

Reaction equation

HRID 1758537 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[Br:8][CH2:9][CH:10]=[CH2:11].C(#N)CCC>>[Br-:8].[CH2:11]([N+:6]1[C:5]([CH3:7])=[CH:4][S:3][C:2]=1[CH3:1])[CH:10]=[CH2:9]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 8008ButyronitrileHCID 109342,4-Dimethylthiazole

Product 1

HCID 21287136HCID 21287136, compoundYield 33%

Procedure

2,4-Dimethylthiazole (6.04 g, 0.05 mole), 3-bromopropene (6.6 g, 0.055 mole) and butyronitrile (25 ml) were combined and refluxed for 2 hours. Upon cooling a brown oil solidified into a wet ivory powder (8.15 g) which was collected by filtration. The powder was dissolved in methanol, combined with aqueous potassium bromide to make the bromide salt, treated with decolorizing charcoal and filtered while hot. The filtrate was poured into ethyl ether to force the bromide salt out of solution as an oil. The ethyl ether was decanted and the oil which remained was chilled in a dry ice/acetone bath, filtered and dried at 60° to yield 3.86 g (33%) of the title compound as a solid; m.p. 130° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureUpon cooling a brown oil
  3. filtrationwas collected by filtration
  4. dissolutionThe powder was dissolved in methanol
  5. additiontreated with decolorizing charcoal
  6. filtrationfiltered while hot
  7. additionThe filtrate was poured into ethyl ether
  8. customThe ethyl ether was decanted
  9. temperaturethe oil which remained was chilled in a dry ice/acetone bath
  10. filtrationfiltered
  11. customdried at 60°

Sources & evidence

ORD record
ord-f6522f92eee54529a2cee89de2b0f04e
Source dataset
uspto-grants-1983_02
Patent number
US04374196

Reaction notes

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