2-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carboxylic acid → 2-Formylthiazole-5-carboxylic acid

HRID 458423Notes

Reaction equation

HRID 458423 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:7][C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=1>Cl>[CH:2]([C:6]1[S:7][C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=1)=[O:1]

Participants

3

Reactant 1

HCID 184418922-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 184418962-Formylthiazole-5-carboxylic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-(1,3-dioxolan-2-yl)-1,3-thiazole-5-carboxylic acid (1.40 g, 6.96 mmol) was dissolved in 15 mL of 6N HCl and heated to reflux for 30 min and then cooled to ambient temperature. The organics were extracted twice with EtOAc and then dried(Na2SO4), filtered and concentrated to give the title compound (1.00 g, 6.36 mmol, 91% yield) as an orange solid. 1H NMR (CDCl3, 400 MHz) δ 10.0 (s, 1H), 8.66 (s, 1H), 6.70–6.00 (bs, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. extractionThe organics were extracted twice with EtOAc
  4. filtrationdried(Na2SO4), filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b805159e456a4d82a2ccd748f1b83963
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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