Acetone → 3-Ethyl-2-{(4-methyl-2H-chromen-2-ylidene)methyl}-benzothiazolium perchlorate

HRID 986376Notes

Reaction equation

HRID 986376 reaction equation
[CH2:1]([N+:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]=1[CH3:12])[CH3:2].[CH3:13][C:14]1[CH:15]=[CH:16][C:17](S(O)(=O)=O)=[CH:18][CH:19]=1.[CH3:24]O.[Cl:26]([OH:30])(=[O:29])(=[O:28])=[O:27].[CH3:31][C:32](C)=[O:33]>>[Cl:26]([O-:30])(=[O:29])(=[O:28])=[O:27].[CH2:1]([N+:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]=1[CH:12]=[C:32]1[CH:31]=[C:13]([CH3:24])[C:14]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:33]1)[CH3:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 24247Perchloric AcidHCID 867451383-Ethyl-2-methyl-1,3-benzothiazol-3-ium;4-methylbenzenesulfonic acid

Product 1

HCID 1317154183-Ethyl-2-{(4-methyl-2H-chromen-2-ylidene)methyl}-benzothiazolium perchlorateYield 40%

Conditions

Temperature
150 °C

Procedure

17.5 g of 3-ethyl-2-methylbenzothiazolium-p-toluenesulfonate and 8.8 g of 4-methylcoumarin-2-thione were reacted under heat at 150° C. for 15 hours, and 20 ml of methanol and 40 ml of acetone were then added to the reaction mixture in the order listed to obtaina uniform solution. After cooling to room temperature, 15.7 g of 60%-perchloric acid was added thereto and stirred at room temperature, whereby crystals precipitated out. The crystals formed were filtered out and washed with a small amount of acetone, and thereafter the crystals were placed in a mixed solvent comprising 20 ml of methanol and 40 ml of acetone at room temperature and stirred for 30 minutes. Then the crystals were again separated by filtration and washed with acetone, to finally obtain 8.5 g of the desired perchlorate product. Yield: 40%. Appearance: brown crystal. M.p.: above 280° C. (decomposition).

Workup

  1. temperatureAfter cooling to room temperature
  2. customwhereby crystals precipitated out
  3. customThe crystals formed
  4. filtrationwere filtered out
  5. washwashed with a small amount of acetone
  6. customwere placed in a mixed solvent comprising 20 ml of methanol and 40 ml of acetone at room temperature
  7. stirringstirred for 30 minutes
  8. customThen the crystals were again separated by filtration
  9. washwashed with acetone, to finally obtain 8.5 g of the desired perchlorate product

Sources & evidence

ORD record
ord-2c969d06f7544bb788aa32466123cb33
Source dataset
uspto-grants-1987_12
Patent number
US04713316

Reaction notes

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