Hydrochloric Acid → 1-(2-Thioxo-2,3-dihydrobenzo[d]thiazol-5-yl)ethanone

HRID 1595167Notes

Reaction equation

HRID 1595167 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10](Cl)=[N:9][C:8]=2[CH:13]=1)(=[O:3])[CH3:2].[SH2:14].[K].Cl>C(O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10](=[S:14])[NH:9][C:8]=2[CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 217036431-(2-Chlorobenzo[d]thiazol-5-yl)ethanoneHCID 86743134Potassium hydrogensulfide

Product 1

HCID 217036441-(2-Thioxo-2,3-dihydrobenzo[d]thiazol-5-yl)ethanoneYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-acetyl-2-chlorobenzothiazole (137 mg, 0.65 mmol), potassium hydrogen sulfide (94 mg, 1.30 mmol) and ethanol (3.3 mL) in a capped flask was stirred in an oil bath at 80° C. for two hours. The mixture was cooled in ice, acidified with 1N hydrochloric acid (1.35 mL) and evaporated in vacuo. The residue was partitioned between water (25 mL) and ethyl acetate (50, 25 mL). The organic extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo to a solid (133 mg). This material was triturated with ether and dried to provide 5-acetyl-2-thioxo-2,3-dihydrobenzothiazole (110 mg) as a pale yellow solid.

Workup

  1. temperatureThe mixture was cooled in ice
  2. customevaporated in vacuo
  3. customThe residue was partitioned between water (25 mL) and ethyl acetate (50, 25 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a solid (133 mg)
  8. customThis material was triturated with ether
  9. customdried

Sources & evidence

ORD record
ord-9b36e4436751483e9091064a182868fc
Source dataset
uspto-grants-2001_09
Patent number
US06288054B1

Reaction notes

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