2-Propanone, 1-(acetyloxy)-3-chloro- → 3-acetoxy-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate

HRID 1722076Notes

Reaction equation

HRID 1722076 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[S:13])[S-:12].C([NH+](CC)CC)C.[C:21]([O:24][CH2:25][C:26]([CH2:28]Cl)=[O:27])(=[O:23])[CH3:22]>C(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[S:12])[S:13][CH2:28][C:26](=[O:27])[CH2:25][O:24][C:21](=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 16413959N,N-diethyl-1-ethanaminium N-(2,3,4-trifluorophenyl)carbamodithioate

Product 1

HCID 200303133-acetoxy-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylammonium N-(2,3,4-trifluorophenyl)dithiocarbamate (2.15 g) prepared in the same manner as in Reference Example 1 was added to methylene chloride (30 ml) and thereto 1-acetoxy-3-chloroacetone (1.0 g) was added dropwise at 2° to 7° C. with stirring over a period of 10 minutes. The mixture was stirred for 20 minutes and washed with 3N hydrochloric acid and then with water. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane-ethyl acetate to give the title compound (1.43 g) as colorless crystals.

Workup

  1. stirringThe mixture was stirred for 20 minutes
  2. washwashed with 3N hydrochloric acid
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of hexane-ethyl acetate

Sources & evidence

ORD record
ord-9181bdc39a794827a5243d0c42f727d9
Source dataset
uspto-grants-1989_08
Patent number
US04853469

Reaction notes

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