Ethanol → ETHYL 2-PHENYLTHIAZOLE-5-CARBOXYLATE

HRID 896470Notes

Reaction equation

HRID 896470 reaction equation
[CH:1]([CH:3](Cl)[C:4]([O-:6])=[O:5])=O.[C:8]([NH2:16])(=[S:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:17][CH2:18]O>>[C:9]1([C:8]2[S:15][C:3]([C:4]([O:6][CH2:17][CH3:18])=[O:5])=[CH:1][N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 683563ThiobenzamideHCID 22350456HCID 22350456, compound

Product 1

HCID 9899456ETHYL 2-PHENYLTHIAZOLE-5-CARBOXYLATEYield 15%

Procedure

A solution of α-formyl-α-chloroacetate (9.34 g, 49.5 mmol, 1 eq) and thiobenzamide (6.79 g, 49.5 mmol, 1 eq) in EtOH (37.0 mL) is refluxed for 1 hr. The solution changes from an orange/brown color to a deep green. This solution is washed with water and extracted with CH2Cl2. The organic fraction is dried over Na2SO4, filtered, and the solvent removed in vacuo. The product is purified by column chromatography using a Biotage Flash 40M column (20% hexanes/EtOAc) to give ethyl 2-phenyl-thiazole-5-carboxylate as a deep orange oil (1.82 g, 15%). MS (ESI) for C12H13NO3S m/z 252.1 (M+H)+.

Workup

  1. washThis solution is washed with water
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic fraction is dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-59fea044953b46aebe8c3449debb8611
Source dataset
uspto-grants-2005_07
Patent number
US06919359B2

Reaction notes

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