p-Toluenesulfonic acid → 7-Dimethoxymethylbenzo-1,2,3-thiadiazole

HRID 257144Notes

Reaction equation

HRID 257144 reaction equation
[CH:1]([C:3]1[C:11]2[S:10][N:9]=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:2].[C:12]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:23](=[O:26])([O-])[O-].[K+].[K+]>CO>[CH3:12][O:2][CH:1]([O:26][CH3:23])[C:3]1[C:11]2[S:10][N:9]=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 14835681Benzo[d][1,2,3]thiadiazole-7-carbaldehyde

Product 1

HCID 200964537-Dimethoxymethylbenzo-1,2,3-thiadiazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.3 g of 7-formylbenzo-1,2,3-thiadiazole in 50 ml of methanol and 0.2 g of p-toluenesulfonic acid is refluxed for 6 hours in a Soxhlet apparatus charged with a molecular sieve A4. The mixture is then cooled, rendered basic using solid potassium carbonate, filtered through Hyflo and evaporated. The residue is purified on silica gel using hexane/ethyl acetate (1:1), resulting in the title compound of refractive index nD21 =1.5750.

Workup

  1. temperatureThe mixture is then cooled
  2. filtrationfiltered through Hyflo
  3. customevaporated
  4. customThe residue is purified on silica gel

Sources & evidence

ORD record
ord-8ffff30f719f43be91465b474070fe20
Source dataset
uspto-grants-1993_11
Patent number
US05260423

Reaction notes

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