Chloranil → HCID 68629706, compound

HRID 1847215Notes

Reaction equation

HRID 1847215 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5](=[C:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6](=O)[CH3:7])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19].ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:16][S:19][C:6]=1[CH3:7])=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 8371ChloranilHCID 14817Phosphorus sulfide (P2S5)HCID 178471717HCID 178471717, compound

Product 1

HCID 68629706HCID 68629706, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the 2-(amino-phenyl-methylene)-3-oxo-butyric acid ethyl ester (41 g, 170 mmol) in toluene (340 mL) were added P2S5 (117.3 g, 520 mmol) and tetrachloro-1,4-benzoquinone (43.2 g, 170 mmol) at r.t. with stirring. The mixture was then refluxed with stirring for 15 min. After cooling to r. t. the mixture was filtered and the filtrate was concentrated to give a brown oil, which was purified by flash column chromatography on silica gel. Elution with 5-35% EtOAc/hexanes gave the title compound as a reddish oil (16.7 g): MS (m/z) 248.2 (M+1).

Workup

  1. temperatureThe mixture was then refluxed
  2. stirringwith stirring for 15 min
  3. temperatureAfter cooling to r
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customto give a brown oil, which
  7. customwas purified by flash column chromatography on silica gel
  8. washElution with 5-35% EtOAc/hexanes

Sources & evidence

ORD record
ord-6c046363603d4b7ca9929c3e3008cd11
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

Loading…