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

HRID 373912Notes

Reaction equation

HRID 373912 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) is added to methylene chloride (100 ml), and thereto is added triethylammonium N-(2,3,4-trifluorophenyl)dithiocarbamate (cf. European Patent Publication 286089) (5.0 g) with stirring at 2° to 5° C. The mixture is stirred for additional 60 minutes and then washed with 3N hydrochloric acid and water in this order. The organic layer is dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue is crystallized from a mixture of hexane-ethyl acetate-ether to give the title compound (4.2 g).

Workup

  1. stirringThe mixture is stirred for additional 60 minutes
  2. washwashed with 3N hydrochloric acid and water in this order
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue is crystallized from a mixture of hexane-ethyl acetate-ether

Sources & evidence

ORD record
ord-27156308282449b38940998559bfb6c4
Source dataset
uspto-grants-1992_11
Patent number
US05166203

Reaction notes

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