Triethylamine → HCID 76011054, compound

HRID 2172834Notes

Reaction equation

HRID 2172834 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:2]1=[S:3].[O:12]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(#N)C>[O:6]=[C:5]1[C:7](=[CH:23][C:22]2[CH:25]=[CH:26][C:19]([O:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:20][CH:21]=2)[S:1][C:2](=[S:3])[N:4]1[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 661394-PhenoxybenzaldehydeHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-

Product 1

HCID 76011054HCID 76011054, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of rhodanine-3-acetic acid (1.00 g) in acetonitrile (20 ml) were added 4-phenoxybenzaldehyde (1.14) and triethylamine (1.06 g), and the mixture was heated with reflux overnight. The reaction solution was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate (50 ml). The solution was washed successively with 1N hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to give [4-oxo-5-(4-phenoxybenzylidene)-2-thioxo-thiazolidin-3-yl]acetic acid (1.20 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux overnight
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. dissolutionthe obtained residue was dissolved in ethyl acetate (50 ml)
  5. washThe solution was washed successively with 1N hydrochloric acid and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-2688b6cd5a8542ec9c882fe3166effd5
Source dataset
uspto-grants-2015_06
Patent number
US09056862B2

Reaction notes

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