Thiophenol → HCID 54462273, compound

HRID 2419508Notes

Reaction equation

HRID 2419508 reaction equation
[Na].[C:2]1([SH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(S[C:12]([CH3:22])([CH3:21])[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:14])C>C(O)C>[C:2]1([S:8][C:12]([CH3:21])([CH3:22])[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 5360545SodiumHCID 53934448HCID 53934448, compound

Product 1

HCID 54462273HCID 54462273, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 11.5 g of metallic sodium dissolved in 250 ml of ethanol, 55 g of thiophenol was added, and then ethanol was distilled off. After adding 400 ml of formamide to the residue to form a uniform solution, the solution was immersed in an ice bath, and to the solution 119 g of ethyl (2-ethylthio2-methylpropionyl)acetate was gradually added. After the completion of the addition, the reaction mixture was removed from the ice bath and stirred for three hours. The reaction mixture was poured into one liter of water and extracted twice, each time with 800 ml of diethyl ether. The extract was washed with a saturated aqueous sodium chloride solution and dried with anhydrous sodium carbonate. After distilling off the diethyl ether, the residue was recrystallized from n-hexane to obtain 112 g (yield 84%) of the intended compound having a melting point of 44° to 45° C.

Workup

  1. distillationethanol was distilled off
  2. additionAfter adding 400 ml of formamide to the residue
  3. customto form a uniform solution
  4. customthe solution was immersed in an ice bath
  5. additionAfter the completion of the addition
  6. customthe reaction mixture was removed from the ice bath
  7. additionThe reaction mixture was poured into one liter of water
  8. extractionextracted twice
  9. washThe extract was washed with a saturated aqueous sodium chloride solution
  10. dry with materialdried with anhydrous sodium carbonate
  11. distillationAfter distilling off the diethyl ether
  12. customthe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-86a3627720f2400fa819f01efee062a7
Source dataset
uspto-grants-1978_08
Patent number
US04106942

Reaction notes

Loading…