Hydrochloric Acid → HCID 178468679, compound

HRID 864976Notes

Reaction equation

HRID 864976 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-7bcd3558c867496dbba1b63675dae8dc
Source dataset
uspto-grants-1996_10
Patent number
US05565445

Reaction notes

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