Acetone → HCID 73186994, compound

HRID 986378Notes

Reaction equation

HRID 986378 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.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[S:20][C:19]([CH3:21])=[N+:18]([CH2:22][CH3:23])[C:17]=2[CH:24]=1.[CH3:25]O.[CH3:27][C:28](C)=[O:29]>C(OCC)(=O)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([O-:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[S:20][C:19]([CH:21]=[C:28]3[CH:27]=[C:11]([CH3:25])[C:1]4[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=4)[O:29]3)=[N+:18]([CH2:22][CH3:23])[C:17]=2[CH:24]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 887MethanolHCID 1130905-Chloro-3-ethyl-2-methylbenzothiazolium p-toluenesulphonate

Product 1

HCID 73186994HCID 73186994, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

11.1 g of 5-chloro-3-ethyl-2-methylbenzothiazolium p-toluenesulfonate and 5.5 g of 4-methylcoumarin-2-thione were reacted under heat at 150° C. for 23 hours, and then 25 ml of methanol, 50 ml of acetone and 150 ml of ethyl acetate were added to the reaction mixture in the order listed. After cooling to room temperature, crystals precipitated out from the reaction solution, and the crystals were separated by filtration and washed with a small amount of acetone. Afterwards, the crystals were placed in a mixed solvent comprising 25 ml of methanol, 50 ml of acetone, and 150 ml of ethyl acetate at room temperature, and stirred for 20 minutes, and then the crystals was again separated by filtration and washed with acetone, to finally obtain 7.9 g of the desired p-toluenesulfonate product. Yield: 52%. Appearance: brown crystal. M.p.: 282°-283° C. (decomposition).

Workup

  1. temperatureAfter cooling to room temperature
  2. customcrystals precipitated out from the reaction solution
  3. customthe crystals were separated by filtration
  4. washwashed with a small amount of acetone
  5. customwere placed in a mixed solvent comprising 25 ml of methanol, 50 ml of acetone, and 150 ml of ethyl acetate at room temperature
  6. customthe crystals was again separated by filtration
  7. washwashed with acetone, to finally obtain 7.9 g of the desired p-toluenesulfonate product

Sources & evidence

ORD record
ord-d62eca8db4264c7e88d4b1734a028386
Source dataset
uspto-grants-1987_12
Patent number
US04713316

Reaction notes

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