Toluene → HCID 178472963, compound

HRID 1196964Notes

Reaction equation

HRID 1196964 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].O=[C:9]([CH3:25])[CH:10]=[CH:11][C:12]1[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=1[O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])(=O)C.[NH4+].C1(C)C=CC=CC=1>O>[O:6]=[C:5]1[CH:7]=[SH:1](=[C:9]([CH3:25])[CH:10]=[CH:11][C:12]2[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=2[O:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:2](=[S:3])[NH:4]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 517165Ammonium AcetateHCID 1201546RhodanineHCID 53986305HCID 53986305, compound

Product 1

HCID 178472963HCID 178472963, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.33 g (0.01 mol) of rhodanine, 2.48 g (0.01 mol) of ethyl 2-(3-oxo-1-butenyl]phenoxyacetate, 0.77 g (0.01 mol) of ammonium acetate and 20 ml of toluene was heated under reflux for 3 hours. After cooling, 100 ml of water were added to the reaction mixture which was extracted with ethyl acetate (3×100 ml). The ethyl acetate layer was washed twice with water and once with a saturated saline solution, dried and concentrated under reduced pressure to give orange crystals. The crystals were purified by silica gel column chromatography (eluent, chloroform : ethyl acetate) to obtain ethyl 2-[3-(4-oxo-2-thioxo-5-thiazolinylidene)-1-butenyl]phenoxyacetate (35.8% yield) from the first eluate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionwas extracted with ethyl acetate (3×100 ml)
  5. washThe ethyl acetate layer was washed twice with water and once with a saturated saline solution
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give orange crystals
  9. customThe crystals were purified by silica gel column chromatography (eluent, chloroform : ethyl acetate)

Sources & evidence

ORD record
ord-606e559fca2847f7bc9a32cbd542348c
Source dataset
uspto-grants-1992_05
Patent number
US05116855

Reaction notes

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