Hydrochloric Acid → HCID 54454167, compound

HRID 2107196Notes

Reaction equation

HRID 2107196 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[S:33])[NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16](=[C:22]3[S:26][C:25](=[S:27])[N:24]([CH2:28][C:29]([OH:31])=[O:30])[C:23]3=[O:32])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:15]=2)=[CH:4][CH:3]=1.[CH2:34](O)[CH3:35].O1CCOCC1.Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[S:33])[NH:10][C:11]2[S:12][CH:13]=[C:14]([C:16](=[C:22]3[S:26][C:25](=[S:27])[N:24]([CH2:28][C:29]([O:31][CH2:34][CH3:35])=[O:30])[C:23]3=[O:32])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:15]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 312751,4-DioxaneHCID 54410075HCID 54410075, compound

Product 1

HCID 54454167HCID 54454167, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 4.8 g of 5-{1-[2-(3-p-chloro-phenylthioureido)thiazol-4-yl]-1-ethoxycarbonylmethylene}-rhodanine-3-acetic acid, 10 g of ethanol and 50 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 sodium chloride solution, and was then dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was recrystallized from a circa 1:1 by volume mixture of hexane and ethyl acetate. The resulting product was an orange powder having the following physical properties.

Workup

  1. waitwas left
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with aqueous sodium chloride solution
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was recrystallized from a circa 1:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-f6a7b31ba73b466ca3ee2273697b4c34
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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