Acetonitrile → p-Toluenesulfonic acid

HRID 986380Notes

Reaction equation

HRID 986380 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.ClC1C=CC2SC(C=C3C=C(C)C4C(=CC=CC=4)O3)=[N+](CC)C=2C=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.ClC1C=CC2SC(SCC)=[N+](CC)C=2C=1.C(#N)C>C(N(CC)CC)C>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 13796806HCID 13796806, compoundHCID 73186994HCID 73186994, compound

Product 1

HCID 6101p-Toluenesulfonic acidYield 211.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5.2 g of 5-chloro-3-ethyl-2-{(4-methyl-2H-chromen-2-ylidene)methyl}-benzothiazolium p-toluenesulfonate and 4.3 g of 5-chloro-3-ethyl-2-ethylthiobenzothiazolium p-toluenesulfonate were added to 140 ml of acetonitrile and dissolved under heat, and then 4.5 ml of triethylamine was added thereto and reacted for 5 minutes. After cooling the precipitated crystals were separated by filtration and recrystallized from a mixed solvent of methanol/chloroform, to obtain 3.6 g of the desired p-toluenesulfonate product. Yield: 50%. Appearance: Brilliant brown crystal. M.p.: above 240° C. (decomposition). ##STR11##

Workup

  1. dissolutiondissolved
  2. temperatureunder heat
  3. customreacted for 5 minutes
  4. temperatureAfter cooling the precipitated crystals
  5. customwere separated by filtration
  6. customrecrystallized from a mixed solvent of methanol/chloroform

Sources & evidence

ORD record
ord-90ebf661d4c44964aea67b2bf5a4aba0
Source dataset
uspto-grants-1987_12
Patent number
US04713316

Reaction notes

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