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

HRID 1085307Notes

Reaction equation

HRID 1085307 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-d20bc25a50ec40979f05ad7e0e32c75e
Source dataset
uspto-grants-1991_04
Patent number
US05008389

Reaction notes

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