Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 86702821, compound

HRID 1850062Notes

Reaction equation

HRID 1850062 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:7]=O)=[CH:5][N:6]=1.[CH2:9]([O:11][C:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13])[CH3:10]>C1COCC1>[NH2:1][C:2]1[S:3][C:4](/[CH:7]=[CH:14]/[C:12]([O:11][CH2:9][CH3:10])=[O:13])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 27377982-Amino-1,3-thiazole-5-carbaldehyde

Product 1

HCID 86702821HCID 86702821, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

2-Aminothiazole-5-carbaldehyde (0.25 g, 2 mmol) was dissolved in anhydrous THF (20 mL). (Ethoxycarbonylmethylene)triphenylphosphorane (0.790 g, 2.2 mmol) was added at room temperature and the reaction mixture was heated overnight at 65° C. The reaction mixture was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography using a gradient of 50-80% EtOAc in Hexanes to provide pure (E)-ethyl 3-(2-aminothiazol-5-yl)acrylate (0.24 g) as a white solid. ES+(M+H)+199.

Workup

  1. customThe reaction mixture was then evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-758ad5703b8f4d4487b68fb53320581c
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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