Allyl bromide → HCID 20061622, compound

HRID 1650740Notes

Reaction equation

HRID 1650740 reaction equation
[O:1]=[C:2]1[NH:6][C:5]([C:7]([F:10])([F:9])[F:8])=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:3]1.[K].[CH2:17](Br)[CH:18]=[CH2:19]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[O:1]=[C:2]1[N:6]([CH2:19][CH:18]=[CH2:17])[C:5]([C:7]([F:8])([F:9])[F:10])=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:3]1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 2783041Ethyl 2-oxo-4-(trifluoromethyl)-2,3-dihydro-1,3-thiazole-5-carboxylateHCID 5462222Potassium

Product 1

HCID 20061622HCID 20061622, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

10 g of ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazolcarboxylate (CA Vol. 92 110 998P), 200 ml of toluene, 2.6 g of potassium in pastilles, 6 ml of allyl bromide and 2.8 g of tetrabutylammonium bromide were heated at 90° C. for 3 hours and the mixture was allowed to return to ambient temperature followed by stirring for 2 hours. The mixture was washed with a N sodium hydroxide solution, with a N hydrochloric acid solution, with water and with a saturated sodium chloride solution. Drying, filtering and concentrating were carried out and the residue was chromatographed on silica and eluted with a hexane-ethyl acetate mixture (9-1) to obtain 8.65 g of the expected product with a Rf=0.25.

Workup

  1. customto return to ambient temperature
  2. washThe mixture was washed with a N sodium hydroxide solution, with a N hydrochloric acid solution, with water and with a saturated sodium chloride solution
  3. customDrying
  4. filtrationfiltering
  5. concentrationconcentrating
  6. customthe residue was chromatographed on silica
  7. washeluted with a hexane-ethyl acetate mixture (9-1)

Sources & evidence

ORD record
ord-43e65f61b68a43a0b21b4e1fac398b48
Source dataset
uspto-grants-1990_05
Patent number
US04925862

Reaction notes

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