Hydrochloric Acid → HCID 178519331, compound

HRID 1736335Notes

Reaction equation

HRID 1736335 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([SH:13])[S:12][C:8]=2[CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1.O>[OH:3][CH2:4][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([SH:13])[S:12][C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 178468679HCID 178468679, compound

Product 1

HCID 178519331HCID 178519331, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-ethoxycarbonyl-2-mercaptobenzothiazole (1.14 g, 4.64 mmol) in anhydrous tetrahydrofuran (14 mL) was heated to reflux under a nitrogen atmosphere and stirred while 1M lithium aluminum hydride in tetrahydrofuran (4.7 mL) was added dropwise. The resulting mixture was stirred and heated at reflux for one hour, then cooled in an ice bath and cautiously treated with 2N hydrochloric acid. The mixture was diluted with water (20 mL) and extracted with ethyl acetate (3×25 mL). The combined extracts were washed with brine (25 mL), dried over sodium sulfate, filtered and evaporated under vacuum to provide 6-hydroxymethyl-2-mercaptobenzothiazole (0.89 g) as a pale yellow solid.

Workup

  1. temperatureto reflux under a nitrogen atmosphere
  2. additionwas added dropwise
  3. temperatureheated
  4. temperatureat reflux for one hour
  5. temperaturecooled in an ice bath
  6. extractionextracted with ethyl acetate (3×25 mL)
  7. washThe combined extracts were washed with brine (25 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-eb7c4f0970a84a789414120d5978cc86
Source dataset
uspto-grants-1996_07
Patent number
US05541176

Reaction notes

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