Ethyl bromoacetate → Ethyl [(4,5-diphenyl-1,3-oxazol-2-yl)thio]acetate

HRID 1414202Notes

Reaction equation

HRID 1414202 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[S:18])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(O)C>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 8536764,5-Diphenyl-4-oxazoline-2-thione

Product 1

HCID 776821Ethyl [(4,5-diphenyl-1,3-oxazol-2-yl)thio]acetateYield 67.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a three-necked, 500 ml flask provided with reflux condenser and mechanical stirrer, 25.3 g 4,5-diphenyl-4-oxazolin-2-thione, 27.6 g anhydrous potassium carbonate, 14.5 ml ethyl bromoacetate and 200 ml absolute ethanol were refluxed for 5 hours with vigorous stirring. The mixture was cooled to room temperature, filtered and washed with absolute ethanol on the filter. The filtrate was evaporated to dryness in vacuo and the residue was suspended in 150 ml ether and 150 ml water. The ethereal phase was separated, dried on anhydrous sodium sulphate, filtered and evaporated to dryness in vacuo to give 23 g ethyl S-(4,5-diphenyloxazol-2-yl)-mercaptoacetate as an oil which was recrystallized from an anhydrous ether-petroleum ether mixture: m.p. 53°-55° C; yield = 67.9%.

Workup

  1. customIn a three-necked, 500 ml flask provided
  2. temperaturewith reflux condenser and mechanical stirrer
  3. filtrationfiltered
  4. washwashed with absolute ethanol on the filter
  5. customThe filtrate was evaporated to dryness in vacuo
  6. customThe ethereal phase was separated
  7. dry with materialdried on anhydrous sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5363ddd828a44ffc9bbe545601c4e794
Source dataset
uspto-grants-1977_01
Patent number
US04001228

Reaction notes

Loading…