1,3-Dichloroacetone → 3-chloro-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate

HRID 1073802Notes

Reaction equation

HRID 1073802 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=[O:4].[F:7][C:8]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:9]=1[NH:16][C:17](=[S:19])[S-:18].C([NH+](CC)CC)C>C(Cl)Cl>[F:7][C:8]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:9]=1[NH:16][C:17](=[S:18])[S:19][CH2:5][C:3](=[O:4])[CH2:2][Cl:1]

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 16413959N,N-diethyl-1-ethanaminium N-(2,3,4-trifluorophenyl)carbamodithioate

Product 1

HCID 100869643-chloro-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamateYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Dichloroacetone (2.0 g) was added to methylene chloride (100 ml) and thereto was added triethylammonium N-(2,3,4-trifluorophenyl)dithiocarbamate (5.0 g) (c.f. European patent publication No. 286089) while stirring at 2° to 5° C. After stirring for 60 minutes, the mixture was washed with 3N HCl and then with water. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The obtained residue was recrystallized from a mixed solvent of hexane - ethyl acetate - ether to give the title compound (4.2 g).

Workup

  1. stirringAfter stirring for 60 minutes
  2. washthe mixture was washed with 3N HCl
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was recrystallized from a mixed solvent of hexane - ethyl acetate - ether

Sources & evidence

ORD record
ord-eda8b7802ed9431fb2e375f5298cb2bc
Source dataset
uspto-grants-1990_11
Patent number
US04971967

Reaction notes

Loading…