Hydrochloric Acid → 7-Methoxymethylbenzo-1,2,3-thiadiazole

HRID 1769971Notes

Reaction equation

HRID 1769971 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[C:13]2[S:12][N:11]=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[H][H].[CH3:16]I.Cl>CS(C)=O.O1CCCC1>[CH3:16][O:3][CH2:4][C:5]1[C:13]2[S:12][N:11]=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 200964331,2,3-Benzothiadiazol-7-ylmethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 200964277-Methoxymethylbenzo-1,2,3-thiadiazole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.4 g of sodium hydride (50% dispersion in oil) in 15 ml of absolute dimethyl sulfoxide are introduced into a reaction vessel, and a solution of 4.15 g of 7-hydroxymethylbenzo-1,2,3-thiadiazole in 15 ml of tetrahydrofuran is added dropwise at 0°-5° C. under a nitrogen atmosphere and with stirring, during which process hydrogen is evolved. After 20 minutes of stirring at 10° C., the mixture is cooled down to 0°-5° C., and a solution of 4 g of methyl iodide in 15 ml of tetrahydrofuran is added dropwise. Stirring is continued for another hour at room temperature, and the mixture is cooled, treated with ice-water, neutralised with dilute hydrochloric acid and extracted with ethyl acetate. The extracts are washed with water, dried over sodium sulfate and evaporated, and the residue is dried in a high vacuum, resulting in the title compound in the form of a yellow oil, nD27 =1.5912.

Workup

  1. stirringAfter 20 minutes of stirring at 10° C.
  2. temperaturethe mixture is cooled down to 0°-5° C.
  3. stirringStirring
  4. waitis continued for another hour at room temperature
  5. temperaturethe mixture is cooled
  6. extractionextracted with ethyl acetate
  7. washThe extracts are washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customthe residue is dried in a high vacuum

Sources & evidence

ORD record
ord-a0dc19274b7e44bda5d288bb7a7daedd
Source dataset
uspto-grants-1995_01
Patent number
US05384321

Reaction notes

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