Hydrochloric Acid → HCID 178509753, compound

HRID 499543Notes

Reaction equation

HRID 499543 reaction equation
C(O)(=O)C[SH:3].[H-].[Na+].Cl[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[N:10]=1.Cl.[C:18]([O:21]CC)(=O)[CH3:19]>CN(C=O)C>[C:15]([C:11]1[N:10]=[C:9]([CH2:19][C:18]([OH:21])=[S:3])[CH:14]=[CH:13][CH:12]=1)#[N:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1184246-Chloropyridine-2-carbonitrile

Product 1

HCID 178509753HCID 178509753, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of thioglycolic acid (6.91 g, 75.0 mmol), sodium hydride (60% in oil, 6.00 g, 150.0 mmol) and DMF (100 ml) was stirred at room temperature for 1 hr. 2-Chloro-6-cyanopyridine (7.00 g, 50.0 mmol) was added thereto, and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was combined with ethyl acetate and 10% hydrochloric acid. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (4.56 g, 47%) as pale yellow crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hrs
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7733d1465a3e4fd9a28e0f762b37c677
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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