Allyl bromide → 2-Allylthio-4,5-bis-(p-methoxyphenyl)-thiazole

HRID 544665Notes

Reaction equation

HRID 544665 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[S:12][C:11](=[S:22])[N:10]=2)=[CH:5][CH:4]=1.[CH2:23](Br)[CH:24]=[CH2:25]>[OH-].[Na+]>[CH2:25]([S:22][C:11]1[S:12][C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1)[CH:24]=[CH2:23]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 132096564,5-Bis-(p-methoxyphenyl)-thiazoline-2-thione

Product 1

HCID 132096752-Allylthio-4,5-bis-(p-methoxyphenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.5 g of 4,5-bis-(p-methoxyphenyl)-thiazoline-2-thione are dissolved in 2.6 ml of 2 N sodium hydroxide solution while stirring. 0.367 g of allyl bromide is added, the mixture is stirred at room temperature for 10 minutes, extracted by shaking twice with 10 ml of toluene each time, the combined aqueous phases are washed twice with 5 ml of 2 N sodium hydroxide solution each time, dried over magnesium sulphate, concentrated by evaporation under reduced pressure and crystallised from hexane. 2-Allylthio-4,5-bis-(p-methoxyphenyl)-thiazole having a melting point of 57°-58° is obtained.

Workup

  1. stirringthe mixture is stirred at room temperature for 10 minutes
  2. extractionextracted
  3. stirringby shaking twice with 10 ml of toluene each time
  4. washthe combined aqueous phases are washed twice with 5 ml of 2 N sodium hydroxide solution each time
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customcrystallised from hexane

Sources & evidence

ORD record
ord-5828c1b0d9d44180b13f046d1f8053a1
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

Loading…