Water → Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylate

HRID 1024428

Reaction equation

HRID 1024428 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][NH:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1.O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:30][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 87949Lawesson's reagentHCID 66572182Ethyl 2-(2-(4-nitrophenyl)-2-oxoethylamino)-2-oxoacetate2×

Product 1

HCID 53404682Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylateYield 73.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Ethyl 2-(2-(4-nitrophenyl)-2-oxoethylamino)-2-oxoacetate (Intermediate 1, step C, 5 g) and Lawesson's reagent (7.22 g) in 1,4-Dioxane (100 ml) was refluxed for 2 hours. The reaction mixture was cooled, water was added and the mixture was neutralized with saturated solution of Na2CO3. This was followed by addition of EtOAc and then the layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to get dark brown residue. The residue was chromatographed on silica gel in 0.5:9.5 EtOAc:CHCl3 to get dark yellow colored solid which was crystallized in CHCl3/pet ether to yield 3.65 g (73%) of the title compound. 1H NMR (CDCl3, 300 MHz): δ 8.33 (d, 2H), 8.3 (s, 1H), 7.83 (d, 2H), 4.54 (q, 2H), 1.49 (t, 3H); MS (ES+) m/z 279 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto get dark brown residue
  7. customThe residue was chromatographed on silica gel in 0.5:9.5 EtOAc
  8. customCHCl3 to get dark yellow colored solid which
  9. customwas crystallized in CHCl3/pet ether

Sources & evidence

ORD record
ord-768940d956a8419c9a984d241c5ef41d
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Linked notes

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