Hydrochloric Acid → HCID 178468679, compound

HRID 1735716Notes

Reaction equation

HRID 1735716 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.S.[K].[S:18]1C2C=CC=CC=2N=C1.Cl>C(O)C>[CH2:14]([O:13][C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([SH:18])[S:3][C:4]=2[CH:10]=1)=[O:12])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7222BenzothiazoleHCID 12067225Ethyl 2-bromo-6-benzothiazolecarboxylateHCID 86743134Potassium hydrogensulfide

Product 1

HCID 178468679HCID 178468679, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The crude 2-bromo-6-ethoxycarbonylbenzothiazole (1.90 g, 6.64 mmol) from Step 2 was suspended in absolute ethanol (35 mL) and treated with potassium hydrogen sulfide (0.96 g, 13.3 mmol). The mixture was placed under a nitrogen atmosphere, stirred, and heated in an oil bath at 80° C. The benzothiazole starring material gradually went into solution. After hearing for 30 minutes, the mixture was cooled in an ice bath, treated with 1N hydrochloric acid (13.5 mL), and evaporated under vacuum. The residue was partitioned between ethyl acetate (100 mL) and water (100 mL) and the aqueous phase extracted with more ethyl acetate (50 mL). The combined ethyl acetate solution was washed with brine (50 mL), dried over sodium sulfate, filtered and evaporated under vacuum to a yellow-tan solid (1.56 g). This material was triturated with diethyl ether and dried under vacuum to provide 6-ethoxycarbonyl-2-mercaptobenzothiazole (1.14 g) as a pale tan powder.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customevaporated under vacuum
  3. customThe residue was partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. extractionthe aqueous phase extracted with more ethyl acetate (50 mL)
  5. washThe combined ethyl acetate solution was washed with brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum to a yellow-tan solid (1.56 g)
  9. customThis material was triturated with diethyl ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-7098db7632f847ec9dacbaa9ba87094d
Source dataset
uspto-grants-1996_07
Patent number
US05538964

Reaction notes

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