Dibromomethane → Methyl 2-(1,3-dithietan-2-ylidene)-2-[N-(4-fluorophenyl)carbamoyl]acetate

HRID 1029795Notes

Reaction equation

HRID 1029795 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:10])=[CH:4][CH:3]=1.[C:16](=[S:18])=[S:17].[OH-].[Na+].Br[CH2:22]Br>CC(C)=O>[S:17]1[CH2:22][S:18][C:16]1=[C:11]([C:9](=[O:10])[NH:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 19901127Methyl 3-(4-fluoroanilino)-3-oxopropanoate

Product 1

HCID 19901140Methyl 2-(1,3-dithietan-2-ylidene)-2-[N-(4-fluorophenyl)carbamoyl]acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 2-[N-(4-fluorophenyl)carbamoyl]acetate (10 g), carbon disulfide (3.2 ml) and acetone (200 ml) was cooled to 5°-10° C., to which 50% aqueous sodium hydroxide (4.2 ml) was added dropwise. The mixture was stirred at same temperature for 2 hrs, then dibromomethane (4 ml) was added dropwise and the reaction mixture was stirred at room temperature for 1 hr and refluxed for 2 hrs. The solid was removed by filtration and the filtrate was poured onto ice-water. The solid formed was filtered, and dissolved in methylene chloride. The solution was washed with 10% aqueous sodium hydroxide solution and water, then dried. The solvent was evaporated and the residue was purified with ethyl acetate and ethyl ether to give the titled compound as a white solid. (8.5 g, 60%).

Workup

  1. additionwas added dropwise
  2. stirringthe reaction mixture was stirred at room temperature for 1 hr
  3. temperaturerefluxed for 2 hrs
  4. customThe solid was removed by filtration
  5. additionthe filtrate was poured onto ice-water
  6. customThe solid formed
  7. filtrationwas filtered
  8. dissolutiondissolved in methylene chloride
  9. washThe solution was washed with 10% aqueous sodium hydroxide solution and water
  10. customdried
  11. customThe solvent was evaporated
  12. customthe residue was purified with ethyl acetate and ethyl ether

Sources & evidence

ORD record
ord-f3070aff3bcd4edcb65da43b69783692
Source dataset
uspto-grants-1992_04
Patent number
US05103013

Reaction notes

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