p-Toluenesulfonic acid → HCID 178455667, compound

HRID 262022Notes

Reaction equation

HRID 262022 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[CH2:10]([S:14][S:15][CH2:16][C:17](=[CH2:19])[CH3:18])[C:11](=[CH2:13])[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH2:10]([S:14][S:15][CH2:16][C:17](=[CH2:18])[CH3:19])[C:11](=[CH2:12])[CH3:13].[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 529081HCID 529081, compoundHCID 178418385HCID 178418385, compound

Product 1

HCID 178455667HCID 178455667, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Benzotriazole (11.9 g.), methallyl disulfide (8.7 g.) and p-toluenesulfonic acid (0.1 g.) in about 75 ml. of xylene were heated, forming a clear homogeneous solution. This solution was heated for more than 12 hr. at 145° C. while small aliquot samples were withdrawn periodically and examined by gas chromatography. The appearance of addition products peaks was observed concurrently with the consumption of the reactants, benzotriazole and methallyl disulfide. Xylene solvent was removed by rotary evaporation. The residue was distilled in a Kugelrohr apparatus at less than 0.1 mm. of mercury pressure. A small amount of distillate product (1 g.) was collected; the residue mixture of products was a dark amber very viscous oil. The infrared spectrum of the reaction product mixture showed the doublet absorption (1385, 1375 cm-1) and the substantial disappearance of the strong terminal vinyl C--H deformation band (900 cm -1) both indicating addition to the olefin groups of the reactant methallyl disulfide.

Workup

  1. customforming a clear homogeneous solution
  2. temperatureThis solution was heated for more than 12 hr
  3. customat 145° C. while small aliquot samples were withdrawn periodically
  4. additionThe appearance of addition products peaks
  5. customwas observed concurrently with the consumption of the reactants, benzotriazole and methallyl disulfide
  6. customXylene solvent was removed by rotary evaporation
  7. distillationThe residue was distilled in a Kugelrohr apparatus at less than 0.1 mm
  8. distillationA small amount of distillate product (1 g.) was collected
  9. additionthe residue mixture of products
  10. customthe doublet absorption (1385, 1375 cm-1)
  11. additionthe substantial disappearance of the strong terminal vinyl C--H deformation band (900 cm -1) both indicating addition to the olefin groups of the reactant methallyl disulfide

Sources & evidence

ORD record
ord-d295a338a5eb45bfb449a21829c23523
Source dataset
uspto-grants-1979_05
Patent number
US04153563

Reaction notes

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