Ethyl Acetate → Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate

HRID 896862Notes

Reaction equation

HRID 896862 reaction equation
Cl[CH:2]([C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:16][C:17]([NH2:19])=[S:18].CCOC(C)=O>CCO>[NH2:19][C:17]1[S:18][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:16]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2723790ThioureaHCID 9855991Ethyl 2-chloro-3-oxo-3-phenylpropanoate

Product 1

HCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-chloro-3-oxo-3-phenylpropanoate (Example 23, 9.73 mmol) and thiourea (9.73 mmol) in EtOH (25 mL) was heated at reflux overnight. The resulting mixture was concentrated in vacuo, neutralized with 18M—NH4OH, and extracted with CH2Cl2. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to afford a yellow solid that was washed with MeOH (3 mL) and dried to afford the product in 89% yield as a pale yellow solid. MH+=249.1, Rf=0.29 (Hexanes:EtOAc=1:1). MH+=249.1, retention time (LC-MS)=2.37 min.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. extractionextracted with CH2Cl2
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto afford a yellow solid
  8. washthat was washed with MeOH (3 mL)
  9. customdried
  10. customto afford the product in 89% yield as a pale yellow solid

Sources & evidence

ORD record
ord-88ef729c969a404a9c7e2723a40348db
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

Loading…