Hydrochloric Acid → HCID 57860414, compound

HRID 1947114Notes

Reaction equation

HRID 1947114 reaction equation
[O-]CC.[Na+].[C:5]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:6][SH:7].[Cl:12][C:13]1[C:18]([C:19](OCC)=[O:20])=[C:17](Cl)[C:16]([CH3:25])=[C:15]([CH3:26])[N:14]=1.Cl>C(O)C>[Cl:12][C:13]1[C:18]2[C:19]([OH:20])=[C:6]([C:5]([O:9][CH2:10][CH3:11])=[O:8])[S:7][C:17]=2[C:16]([CH3:25])=[C:15]([CH3:26])[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 127496743-Pyridinecarboxylic acid, 2,4-dichloro-5,6-dimethyl-, ethyl ester

Product 1

HCID 57860414HCID 57860414, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 20% solution (1.73 g, 5.08 mmol) of sodium ethoxide in ethanol was diluted with ethanol (5 mL), and ethyl thioglycolate (610 mg, 5.08 mmol) was added. Ethyl 2,4-dichloro-5,6-dimethylpyridine-3-carboxylate (630 mg, 2.54 mmol) was added to the mixture, and the mixture was stirred at room temperature for 18 hr. 2N Hydrochloric acid (3 mL) was added to the reaction mixture and the mixture was partitioned between brine and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The obtained solid was washed with diisopropyl ether-hexane, and dried under reduced pressure to give the title compound (374 mg, 52%) as a white powder.

Workup

  1. additionwas added
  2. customthe mixture was partitioned between brine and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe obtained solid was washed with diisopropyl ether-hexane
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-127fb91e6f1f4fcd8b7014b5428a8901
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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