Hydrochloric Acid → HCID 19041003, compound

HRID 1683779Notes

Reaction equation

HRID 1683779 reaction equation
[OH-].[Na+].O.[CH2:4]([O:6][C:7]1[CH:8]=[C:9]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28]([O:30]CC)=[O:29])[N:22]=3)[N:20]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:5].Cl>C(O)C>[CH2:4]([O:6][C:7]1[CH:8]=[C:9]([C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28]([OH:30])=[O:29])[N:22]=3)[N:20]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 19041124HCID 19041124, compound

Product 1

HCID 19041003HCID 19041003, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.32 g of sodium hydroxide dissolved in 20 ml of ethanol and 20 ml of water was added to 0.54 g of 2-(3,4-diethoxyphenyl)-4-(5-hydroxy-6-ethoxycarbonyl-2-pyridyl)thiazole. The mixture was refluxed for 2.5 hours. To the reaction mixture was added 100 ml of water. The mixture was made acidic with concentrated hydrochloric acid and subjected to extraction four times with 70 ml of ethyl acetate. The solvent in the extract was removed and the resulting residue was recrystallized from ethyl acetate-diethyl ether to obtain 0.24 g of 2-(3,4-diethoxyphenyl)-4-(5-hydroxy-6-carboxy-2-pyridyl)thiazole. m.p.: 161.4°-162° C.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. extractionsubjected to extraction four times with 70 ml of ethyl acetate
  3. customThe solvent in the extract was removed
  4. customthe resulting residue was recrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-2e1bc94e907a47799b659c08289068da
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Reaction notes

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