Hydrochloric Acid → HCID 21703645, compound

HRID 1595165Notes

Reaction equation

HRID 1595165 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[S:18][C:17](=[S:19])[NH:16][C:15]=2[CH:20]=1)(O)=[O:8].Cl>O1CCCC1.O>[OH:8][CH2:7][CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[S:18][C:17](=[S:19])[NH:16][C:15]=2[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 21703647(2-Sulfanylidene-2,3-dihydro-1,3-benzothiazol-5-yl)acetic acid

Product 1

HCID 21703645HCID 21703645, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride (65 mL of a 1M tetrahydrofuran solution, 0.065 mol) was added dropwise over 15 min to a mechanically stirred and refluxing solution of 5-carboxymethyl-2-thioxo-2,3-dihydrobenzothiazole (11.27 g, 0.050 mol) in anhydrous tetrahydrofuran (150 mL). The resulting mixture was stirred at reflux for 90 min then cooled in an ice-bath and cautiously treated with 2N hydrochloric acid (250 mL). The resulting mixture was diluted with water (250 mL) and extracted three times with ethyl acetate (250, 250, and 150 mL). The combined extracts were washed with brine (2×200 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to approximately 140 mL volume. Some solid was present at this point. The mixture was diluted with ether (100 mL) and filtered. The filter cake was washed with ether and dried in vacuo to afford 5-(2-hydroxyethyl)-2-thioxo-2,3-dihydrobenzothiazole (8.58 g) as pale tan crystals.

Workup

  1. stirringThe resulting mixture was stirred
  2. temperatureat reflux for 90 min
  3. temperaturethen cooled in an ice-bath
  4. extractionextracted three times with ethyl acetate (250, 250, and 150 mL)
  5. washThe combined extracts were washed with brine (2×200 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to approximately 140 mL volume
  9. additionThe mixture was diluted with ether (100 mL)
  10. filtrationfiltered
  11. washThe filter cake was washed with ether
  12. customdried in vacuo

Sources & evidence

ORD record
ord-bb8a582cff254e4ba784708bcb08a13a
Source dataset
uspto-grants-2001_09
Patent number
US06288054B1

Reaction notes

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