Hydrochloric Acid → HCID 19748893, compound

HRID 1885568Notes

Reaction equation

HRID 1885568 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][NH:23][C:24](=[O:31])[CH2:25][C:26]([O:28]CC)=[O:27])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[OH-].[Na+].CO.Cl>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][NH:23][C:24](=[O:31])[CH2:25][C:26]([OH:28])=[O:27])[S:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 19748896HCID 19748896, compound

Product 1

HCID 19748893HCID 19748893, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4,5-bis(4methoxyphenyl)-2-ethoxycarbonylacetylaminomethylthiazole (0.43 g) and 4N sodium hydroxide (3 ml), methanol (5 ml) and water (5 ml) was stirred at ambient temperature for 4.5 hours. After allowing to cool to room temperature, the mixture was poured to water, and the aqueous layer was adjusted to pH 1 with 10% hydrochloric acid, and extracted with diethyl ether. The organic layer was washed with water and brine, and dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The resulting residue was triturated with isopropyl ether and diethyl ether, to give 4,5-bis(4-methoxyphenyl)-2-(carboxyacetylaminomethyl)thiazole (0.23 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. additiontreated with activated charcoal
  6. filtrationAfter filtration
  7. customthe filtrate was evaporated in vacuo
  8. customThe resulting residue was triturated with isopropyl ether and diethyl ether

Sources & evidence

ORD record
ord-c2629629b17b4991ac534ee5e91c9efe
Source dataset
uspto-grants-1992_09
Patent number
US05145860

Reaction notes

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