Acetone → HCID 73186993, compound

HRID 986377Notes

Reaction equation

HRID 986377 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:12][C:13]([F:27])([F:26])[C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([CH3:22])=[N+:19]([CH2:23][CH3:24])[C:18]=2[CH:25]=1.CC(C)=O.[C:32]([O:35][CH2:36][CH3:37])(=O)[CH3:33]>>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[F:27][C:13]([F:12])([F:26])[C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([CH:22]=[C:36]3[CH:37]=[C:5]([CH3:4])[C:6]4[C:32](=[CH:33][CH:3]=[CH:2][CH:1]=4)[O:35]3)=[N+:19]([CH2:23][CH3:24])[C:18]=2[CH:25]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 22131943HCID 22131943, compound

Product 1

HCID 73186993HCID 73186993, compoundYield 46%

Conditions

Temperature
150 °C

Procedure

2.37 g of 5-trifluoromethyl-3-ethyl-2-methylbenzothiazolium p-toluenesulfonate and 1.0 g of 4-methylcoumarin-2-thione were reacted under heat at 150° C. for 20 hours, and then 10 ml of metrhanol, 10 ml of acetone, and 20 ml of ethyl acetate were added to the reaction mixture in the order listed to obtain a uniform solution. After cooling to room temperature, crystals precipitated out therefrom. The crystals formed were separated by filtration and washed with a small amount of acetone, and thereafter the crystlas were placed in a mixed solvent comprising 10 ml of methanol, 10 ml of acetone, and 20 ml of ethyl acetate at room temperature, and stirred for 40 minutes. Then, the crystals were again taken out by filtration and washed with acetone, at last to obtain 1.47 g of the desired p-toluenesulfonate product. Yield: 46%. Appearance: brown crystal. M.P.: 272°-273° C. (decomposition).

Workup

  1. customto obtain a uniform solution
  2. temperatureAfter cooling to room temperature
  3. customcrystals precipitated out therefrom
  4. customThe crystals formed
  5. customwere separated by filtration
  6. washwashed with a small amount of acetone
  7. customat room temperature
  8. filtrationThen, the crystals were again taken out by filtration
  9. washwashed with acetone

Sources & evidence

ORD record
ord-c80d6d8cff27487584180f625d029aab
Source dataset
uspto-grants-1987_12
Patent number
US04713316

Reaction notes

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