Hydrochloric Acid → HCID 20430559, compound

HRID 2413127Notes

Reaction equation

HRID 2413127 reaction equation
[O:1]=[C:2]1[CH2:7][N:6](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:5][C:4]2[CH:18]=[CH:19][S:20][C:3]1=2.CC(C)([O-])C.[K+].Cl>C(O)(C)(C)C>[OH:1][C:2]1[C:3]2[S:20][CH:19]=[CH:18][C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12751998HCID 12751998, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20430559HCID 20430559, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 7-oxo-5-tosyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (19.6 g; 0.064 mole; obtained in (b) above) and potassium tert-butoxide (28.6 g; 0.255 mole) in tert-butanol (300 ml) is refluxed for 2 hours under a nitrogen atmosphere. Evaporation of the solvent in vacuo leaves a residue which is taken up into 2N hydrochloric acid. The aqueous phase is extracted with ether, made basic by addition of concentrated ammonia, and evaporated to dryness. The residue is extracted four times with boiling ethyl acetate. The organic extracts are filtered through a silica bed and evaporated to dryness. The solid residue is recrystallized from ethanol-acetonitrile. Greyish crystals; M.P.=180° C.; Yield: 72%.

Workup

  1. customEvaporation of the solvent in vacuo
  2. customleaves a residue which
  3. extractionThe aqueous phase is extracted with ether
  4. additionmade basic by addition of concentrated ammonia
  5. customevaporated to dryness
  6. extractionThe residue is extracted four times with boiling ethyl acetate
  7. filtrationThe organic extracts are filtered through a silica bed
  8. customevaporated to dryness
  9. customThe solid residue is recrystallized from ethanol-acetonitrile

Sources & evidence

ORD record
ord-4e2e22798c1045feb3ba95a9bf93cf75
Source dataset
uspto-grants-1985_01
Patent number
US04496568

Reaction notes

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