Chloranil → methyl 5-methyl-3-phenyl-1,2-thiazole-4-carboxylate

HRID 1847286Notes

Reaction equation

HRID 1847286 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4](=[C:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5](=O)[CH3:6].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:18].C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:15][S:18][C:5]=1[CH3:6])=[O:16]

Participants

5

Reactant 3

HCID 8371ChloranilHCID 14817Phosphorus sulfide (P2S5)HCID 178500544HCID 178500544, compound

Product 1

HCID 616242methyl 5-methyl-3-phenyl-1,2-thiazole-4-carboxylateYield 42.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(amino-phenyl-methylene)-3-oxo-butyric acid methyl ester (4.48 mmol), phosphorus pentasulfide (13.43 mmol), chloranil (4.48 mmol), and toluene was refluxed for 15 minutes before it was cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by flash column chromatography with a gradient of ethyl acetate and hexanes on silica gel (40 g) to give the title compound as a red oil (445 mg); 1H NMR (CDCl3, 200 MHz): δ=7.51 (m, 2H), 7.42 (m, 3H), 3.75 (s, 3H), 2.74 (s, 3H); MS: (+) m/z 224.32 (M+H+).

Workup

  1. temperaturewas refluxed for 15 minutes before it
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by flash column chromatography with a gradient of ethyl acetate and hexanes on silica gel (40 g)

Sources & evidence

ORD record
ord-3d29f7f544614a7aaf126f7d1b9e4c01
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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