Ethanol → ETHYL 2-PHENYLTHIAZOLE-5-CARBOXYLATE

HRID 2301870Notes

Reaction equation

HRID 2301870 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>>[CH2:17]([O:6][C:4]([C:3]1[S:15][C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:16][CH:1]=1)=[O:5])[CH3:18]

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 hour. 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 the product 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-2e8c4d1d9ccb4e11b5ef7958de71630f
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

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