HCID 10565635, compound → Ethyl 2-phenoxy-5-thiazolecarboxylate

HRID 2080117Notes

Reaction equation

HRID 2080117 reaction equation
[CH2:1]([O:3][C:4]([C:6]1C(=O)O[N:8]([C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[S:13])[CH:7]=1)=[O:5])[CH3:2]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[S:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 10565635HCID 10565635, compound

Product 1

HCID 13106142Ethyl 2-phenoxy-5-thiazolecarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Oxo-2-phenoxythiocarbonyl-2,5-dihydro-isoxazole-4-carboxylic acid ethyl ester described in Preparation Example 113 (500 mg, 2.01 mmol) was dissolved in acetone (500 mL), and the solution was irradiated with light (300 nm) for 30 minutes at room temperature. The reaction solution was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1), and the title compound (384 mg, 1.54 mmol, 90%) was obtained as a pale yellow oil.

Workup

  1. customthe solution was irradiated with light (300 nm) for 30 minutes at room temperature
  2. customThe reaction solution was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-4e24543b738d4f7fbd775a1c28f6fdd7
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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