Benzyl Bromide → HCID 53945212, compound

HRID 1650744Notes

Reaction equation

HRID 1650744 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.[OH-].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[O:1]=[C:2]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 2783041Ethyl 2-oxo-4-(trifluoromethyl)-2,3-dihydro-1,3-thiazole-5-carboxylate

Product 1

HCID 53945212HCID 53945212, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

5 g of ethyl (2,3-dihydro-2-oxo-4-trifluoromethyl-thiazol-5-yl)-carboxylate (CA Vol. 92 110 998P), 80 ml of toluene, 1.16 g of potassium hydroxide, 3.7 ml of benzyl bromide and 1.61 g of tetrabutyl-ammonium bromide were heated at 70° C. for 7 hours and the mixture was allowed to return to ambient temperature, and was decanted, washed and dried to obtain 7.2 g of product which was chromatographed on silica. Elution with a hexane-isopropyl ether mixture (8-2) yielded 5.46 g of the expected product with a Rf=0.17.

Workup

  1. customto return to ambient temperature
  2. customwas decanted
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-86833b80b88647b3a4fb72472299e059
Source dataset
uspto-grants-1990_05
Patent number
US04925862

Reaction notes

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