Acetone → HCID 70447139, compound

HRID 986379Notes

Reaction equation

HRID 986379 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S([O-])(=O)=O)=[CH:3][CH:2]=1.[CH3:12][O:13][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.[CH3:26]O.[I-:28].[Na+].[CH3:30][C:31](C)=[O:32]>>[I-:28].[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([CH:22]=[C:31]3[CH:30]=[C:11]([CH3:26])[C:1]4[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=4)[O:32]3)=[N+:19]([CH2:23][CH3:24])[C:18]=2[CH:25]=1

Participants

5

Reactant 4

HCID 180Acetone2×HCID 887MethanolHCID 5238Sodium IodideHCID 170645Benzothiazolium, 3-ethyl-5-methoxy-2-methyl-, salt with 4-methylbenzenesulfonic acid (1:1)

Product 1

HCID 70447139HCID 70447139, compoundYield 38%

Conditions

Temperature
150 °C

Procedure

2.15 g of 5-methoxy-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 15 ml of methanol and 12 ml of acetone were added to the reaction mixture to obtain a uniform solution. 1.7 g of sodium iodide (in the form of a solution in 5 ml of acetone) was added dropwise to said solution and stirred at room temperature, whereby crystals precipitated out therefrom. The crystals formed were separated by filtration and washed with a small amount of acetone, and then the crystals were placed in 20 ml of water at room temperature and stirred for 15 minutes. Then, the crystals were again separated by filtration and washed with acetone, to obtain 1.02 g of the desired iodide product. Yield: 38%. Appearance: brown crystal. M.p.: 273°-274° C. (decomposition).

Workup

  1. customto obtain a uniform solution
  2. customwhereby crystals precipitated out therefrom
  3. customThe crystals formed
  4. customwere separated by filtration
  5. washwashed with a small amount of acetone
  6. customwere placed in 20 ml of water at room temperature
  7. stirringstirred for 15 minutes
  8. customThen, the crystals were again separated by filtration
  9. washwashed with acetone

Sources & evidence

ORD record
ord-fdfff96be5ae4f0abc7a8fe7596cbe6b
Source dataset
uspto-grants-1987_12
Patent number
US04713316

Reaction notes

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