Pyridine → 2-n-Propylamino-5-n-propyl thiazole-4-carboxylic acid ethyl ester

HRID 2256202Notes

Reaction equation

HRID 2256202 reaction equation
[CH2:1]([NH:4][C:5]([NH2:7])=[S:6])[CH2:2][CH3:3].[CH2:8]([O:10][C:11](=[O:19])[C:12](=O)[CH:13](Cl)[CH2:14][CH2:15][CH3:16])[CH3:9].N1C=CC=CC=1>C(O)C>[CH2:8]([O:10][C:11]([C:12]1[N:7]=[C:5]([NH:4][CH2:1][CH2:2][CH3:3])[S:6][C:13]=1[CH2:14][CH2:15][CH3:16])=[O:19])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1615208Propyl-2-thioureaHCID 11030654Ethyl 3-chloro-2-oxohexanoate

Product 1

HCID 540564382-n-Propylamino-5-n-propyl thiazole-4-carboxylic acid ethyl esterYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

n-Propylthiourea (270 mg), 3-chloro-2-oxohexanoic acid ethyl ester (441 mg), and pyridine (0.28 ml) were added to ethanol (10 ml), and the solution was refluxed for 3.5 hours. The solvent was evaporated. The residue was extracted with chloroform (20 ml), and washed with dilute hydrochloric acid solution (10 ml). The organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (eluent:chloroform/methanol=100/1), 2-n-propylamino-5-n-propyl thiazole-4-carboxylic acid ethyl ester (400 mg) was obtained.

Workup

  1. temperaturethe solution was refluxed for 3.5 hours
  2. customThe solvent was evaporated
  3. extractionThe residue was extracted with chloroform (20 ml)
  4. washwashed with dilute hydrochloric acid solution (10 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (eluent:chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-522bb2c0464e4c898072f6b233d9a168
Source dataset
uspto-grants-1997_08
Patent number
US05654322

Reaction notes

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