Ethyl p-methylbenzenesulfonate → Benzothiazolium, 3-ethyl-2-methyl-, 4-methylbenzenesulfonate (1:1)

HRID 1089402

Reaction equation

HRID 1089402 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]1([CH3:23])[CH:16]=[CH:15][C:14]([S:17]([O:20]CC)(=[O:19])=[O:18])=[CH:13][CH:12]=1>CC(C)=O>[C:11]1([CH3:23])[CH:12]=[CH:13][C:14]([S:17]([O-:20])(=[O:18])=[O:19])=[CH:15][CH:16]=1.[CH2:11]([N+:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]=1[CH3:1])[CH3:12]

Participants

4

Reactant 2

HCID 6638Ethyl p-methylbenzenesulfonateHCID 84462-Methylbenzothiazole

Product 1

HCID 84711Benzothiazolium, 3-ethyl-2-methyl-, 4-methylbenzenesulfonate (1:1)

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
150 °C

Procedure

300 g (2 mol) of 2-methylbenzothiazole and 440 g (2.2 mol) of ethyl p-toluenesulfonate (or a mixture of ethyl o- and p-toluenesulfonate) are heated with stirring to 150° C., the temperature rising to about 200° C. due to the exothermic reaction. After 10 minutes, the mixture is poured into two liters of acetone, and the product which has precipitated is filtered off with suction, washed with acetone and dried in vacuo. Yield 730 g (98%).

Workup

  1. temperatureare heated
  2. customthe temperature rising to about 200° C. due to the exothermic reaction
  3. customthe product which has precipitated
  4. filtrationis filtered off with suction
  5. washwashed with acetone
  6. customdried in vacuo

Sources & evidence

ORD record
ord-89a1d61946f14c56b89599dd1f2e90c8
Source dataset
uspto-grants-1990_10
Patent number
US04966828

Linked notes

Loading…