Hydrochloric Acid → HCID 57686861, compound

HRID 2367161Notes

Reaction equation

HRID 2367161 reaction equation
[C:1]([C:5]1[S:9][C:8]([C:10](OCC)=[O:11])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[Na+].Cl>CO>[C:1]([C:5]1[S:9][C:8]([CH2:10][OH:11])=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 2757341ethyl 5-tert-butyl-1,3,4-thiadiazole-2-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 57686861HCID 57686861, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g (4.67 mmol) of ethyl 5-tert-butyl-1,3,4-thiadiazole-2-carboxylate is dissolved in 45 mL of methanol and 0.353 g (9.33 mmol) of sodium borohydride is added portionwise, with stirring, at room temperature. The medium is stirred for 1 hour at room temperature and then concentrated under vacuum. The residue obtained is taken up in aqueous solution saturated with sodium chloride. The aqueous solution is brought to ph 7 by slowly adding, with stirring, aqueous 1N hydrochloric acid solution. After stirring for 1 hour at room temperature, the aqueous phase is extracted three times with dichloromethane and the combined organic phases are then washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated to dryness. 0.802 g (100%) of the expected product is obtained in the form of an oil.

Workup

  1. stirringThe medium is stirred for 1 hour at room temperature
  2. concentrationconcentrated under vacuum
  3. customThe residue obtained
  4. additionby slowly adding
  5. stirringwith stirring
  6. stirringAfter stirring for 1 hour at room temperature
  7. extractionthe aqueous phase is extracted three times with dichloromethane
  8. washthe combined organic phases are then washed once with saturated aqueous sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3320c5246c4848bdb1c37abeb7845b8a
Source dataset
uspto-grants-2014_04
Patent number
US08697883B2

Reaction notes

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