Ammonia → 5-{1-Ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine acetic acid

HRID 2107154Notes

Reaction equation

HRID 2107154 reaction equation
[C:1]1([NH:7][C:8](=[O:22])[NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:23]1[CH2:29][C:27](=[O:28])[N:26]([CH2:30][C:31]([OH:33])=[O:32])[C:24]1=[S:25].[Cl-].[NH4+].N.Cl>C(O)C>[CH2:19]([O:18][C:16]([C:15](=[C:29]1[S:23][C:24](=[S:25])[N:26]([CH2:30][C:31]([OH:33])=[O:32])[C:27]1=[O:28])[C:13]1[N:14]=[C:10]([NH:9][C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:22])[S:11][CH:12]=1)=[O:17])[CH3:20]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 15053489Ethyl 2-(3-phenylureido)thiazol-4-ylglyoxylate

Product 1

HCID 541363965-{1-Ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine acetic acidYield 48.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture comprising 1 g of ethyl 2-(3-phenylureido)thiazol-4-ylglyoxylate, 0.59 g of rhodanine-3-acetic acid 0.4 g of ammonium chloride, 0.4 ml of 28% v/v aqueous ammonia and 4 ml of ethanol was stirred at an external temperature of 80° C. for one hour. The reaction mixture was then acidified with dilute hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography, using as eluent a 50:1:1:1 by volume mixture of benzene, ethyl acetate, ethanol and acetic acid. The product thus obtained was recrystallized from acetic acid, giving 0.74 g of the desired compound as a yellow powder.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel column chromatography
  6. additionby volume mixture of benzene, ethyl acetate, ethanol and acetic acid
  7. customThe product thus obtained
  8. customwas recrystallized from acetic acid

Sources & evidence

ORD record
ord-ac2f24662d0741ddaeda4147b38e14cf
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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