1,1-Dichloroacetone → 73765-41-0

HRID 1256913Notes

Reaction equation

HRID 1256913 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[S:10])=[CH:4][CH:3]=1.[Cl:12][CH:13](Cl)[C:14](=O)[CH3:15].C(=O)([O-])O.[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[S:10][CH:15]=[C:14]([CH2:13][Cl:12])[N:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 105671,1-DichloroacetoneHCID 516892Sodium BicarbonateHCID 27348272-(4-chlorophenyl)ethanethioamide

Product 1

HCID 1677789673765-41-0Yield 85.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(4-chlorophenyl)thioacetamide (3.51 g) in 1,4-dioxane (20 mL) were added dichloroacetone (2.64 g) and sodium hydrogen carbonate (1.75 g) at room temperature, and the mixture was stirred for 3 days. Insoluble material was removed by filtration, thionyl chloride (1.52 mL) was added to the filtrate, and the mixture was heated at 70° C. for 30 min. The reaction mixture was adjusted to pH=8-9 by the addition of saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate/hexane (1/1)(100 mL×2). The organic layer was washed with saturated brine, and concentrated under reduced pressure to give the title compound (4.19 g) as a pale-yellow solid.

Workup

  1. customInsoluble material was removed by filtration, thionyl chloride (1.52 mL)
  2. additionwas added to the filtrate
  3. additionThe reaction mixture was adjusted to pH=8-9 by the addition of saturated aqueous sodium hydrogen carbonate solution
  4. extractionextracted with ethyl acetate/hexane (1/1)(100 mL×2)
  5. washThe organic layer was washed with saturated brine
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad363349efe14b1887b7afdf0cf4a78c
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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