Potassium Carbonate → Ethyl 4-methyl-5-phenyl-2-thiazolecarboxylate

HRID 896473Notes

Reaction equation

HRID 896473 reaction equation
[CH3:1][CH:2]([NH:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(Cl)(Cl)Cl.O>[CH3:1][C:2]1[N:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:20][C:3]=1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 86125860HCID 86125860, compound

Product 1

HCID 22350452Ethyl 4-methyl-5-phenyl-2-thiazolecarboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

The product from Step 24b (2.58 g, 10.4 mmol, 1 eq) and P2S5 (4.83 g, 10.9 mmol, 1.05 eq) are suspended in 30 mL CHCl3. The mixture is heated under reflux. After 12 h, water and solid K2CO3 are carefully added until all material dissolves. The aqueous layer is made sufficiently basic with 1N NaOH (pH more than 10) and extracted with EtOAc. The combined organic layers are washed with 1N NaOH and brine, dried over MgSO4, filtered and concentrated to give ethyl 4-methyl-5-phenyl-1,3-thiazole-2-carboxylate as a yellow oil (2.51 g, 98%). MS (ESI) for C13H13NO2S m/z 248.1 (M+H)+.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux
  3. dissolutiondissolves
  4. extractionextracted with EtOAc
  5. washThe combined organic layers are washed with 1N NaOH and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-630af91c313948d7bec3e21f9295568f
Source dataset
uspto-grants-2005_07
Patent number
US06919359B2

Reaction notes

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