Hydrochloric Acid → HCID 86744030, compound

HRID 2107195Notes

Reaction equation

HRID 2107195 reaction equation
[CH2:1]([O:3][C:4]([C:6](=[C:22]1[S:26][C:25](=[S:27])[N:24]([CH2:28][C:29]([OH:31])=[O:30])[C:23]1=[O:32])[C:7]1[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[S:14])[S:10][CH:11]=1)=[O:5])[CH3:2].[CH2:33](O)[CH3:34].O1CCOCC1.Cl>O>[CH2:1]([O:3][C:4]([C:6](=[C:22]1[S:26][C:25](=[S:27])[N:24]([CH2:28][C:29]([O:31][CH2:33][CH3:34])=[O:30])[C:23]1=[O:32])[C:7]1[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[S:14])[S:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 312751,4-DioxaneHCID 53766990HCID 53766990, compound

Product 1

HCID 86744030HCID 86744030, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 10 g of 5-{1-ethoxycarbonyl-1-[2-(3-phenylthioureido)thiazol-4-yl]methylene}rhodanine-3acetic acid 20 g of ethanol and 150 ml of a 4N dioxane solution of hydrogen chloride was left to stand at room temperature for 4.5 days. The reaction mixture was then poured into water and extracted with ethyl acetate. The extract was washed with aqueous potassium carbonate solution and then with aqueous sodium chloride solution, and was then dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography, using as eluent a 1:1 by volume mixture of hexane and ethyl acetate. The resulting crystalline product was recrystallised from a 1:5 by volume mixture of hexane and ethyl acetate, giving a yellow powder having the following physical properties.

Workup

  1. waitwas left
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with aqueous potassium carbonate solution
  4. dry with materialwith aqueous sodium chloride solution, and was then dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. additionby volume mixture of hexane and ethyl acetate
  8. customThe resulting crystalline product was recrystallised from a 1:5 by volume mixture of hexane and ethyl acetate
  9. customgiving a yellow powder

Sources & evidence

ORD record
ord-bc2b9fa15bb945f0bd04edb3f9b8a8b6
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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