Hydrochloric Acid → 5,6-dimethoxybenzo[d]thiazol-2(3H)-one

HRID 223393Notes

Reaction equation

HRID 223393 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:15][CH3:16])=[CH:5][C:6]2[S:10][C:9]([O:11]CC)=[N:8][C:7]=2[CH:14]=1.Cl>C(O)C>[CH3:1][O:2][C:3]1[C:4]([O:15][CH3:16])=[CH:5][C:6]2[S:10][C:9](=[O:11])[NH:8][C:7]=2[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 205222905,6-Dimethoxy-2-ethoxybenzothiazole

Product 1

HCID 205222855,6-dimethoxybenzo[d]thiazol-2(3H)-oneYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

19.7 gm (82 mmols) of 5,6-dimethoxy-2-ethoxybenzothiazole were dissolved in 500 ml of ethanol and admixed dropwise at the boiling point with 64 ml of concentrated aqueous hydrochloric acid. After refluxing the mixture for 3 hours, the solvent was evaporated. The residue was recrystallized from methanol. 8.1 gm (48% of theory) of 5,6-dimethoxy-2(3H)-benzothiazolone having a melting point of 191° C. were obtained.

Workup

  1. temperatureAfter refluxing the mixture for 3 hours
  2. customthe solvent was evaporated
  3. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-9009c3724f124f718391ebc1be46748e
Source dataset
uspto-grants-1982_10
Patent number
US04353919

Reaction notes

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