Tetrahydrofuran → Ethyl 2,4-dimethylthiazole-5-carboxylate

HRID 1624214Notes

Reaction equation

HRID 1624214 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Cl[CH:6]([C:10]([CH3:12])=O)[C:7]([O-:9])=[O:8].O1CC[CH2:15][CH2:14]1>>[CH3:2][C:1]1[S:3][C:6]([C:7]([O:9][CH2:14][CH3:15])=[O:8])=[C:10]([CH3:12])[N:4]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2723949ThioacetamideHCID 219495572-Chloroacetoacetate

Product 1

HCID 603810Ethyl 2,4-dimethylthiazole-5-carboxylate

Conditions

Temperature
80 °C

Procedure

126 mmol of thioacetamide was dissolved in 378 ml of tetrahydrofuran, then a solution, in which 120 mmol of 2-chloroaceto acetate was dissolved in 36 ml of tetrahydrofuran, was gradually dropped with keeping a temperature at 0 to 10° C. using an ice bath. After the dropping, stirring was continued for 1 hour at a room temperature, then the temperature was heated up to 80° C. and the reaction was continued for 3 hours. The reacted liquid was kept still overnight. A recrystallized solid was filtrated, and dissolved in 50 ml of water. Sodium hydrogen carbonate was added until the pH of the solution reached 8 to 9, the product was extracted and separated into an organic layer using ethyl acetate, then dried under sodium sulfate and the solvent was evaporated out, obtaining ethyl 2,4-dimethyl-1,3-thiazole-5-carboxylate.

Workup

  1. additionwas gradually dropped
  2. customat 0 to 10° C.
  3. waitthe reaction was continued for 3 hours
  4. waitThe reacted liquid was kept still overnight
  5. filtrationA recrystallized solid was filtrated
  6. dissolutiondissolved in 50 ml of water
  7. additionSodium hydrogen carbonate was added until the pH of the solution
  8. extractionthe product was extracted
  9. customseparated into an organic layer
  10. customdried under sodium sulfate
  11. customthe solvent was evaporated out

Sources & evidence

ORD record
ord-4c76ecc1c3f94299bb7af52a53fb4b5e
Source dataset
uspto-grants-2014_07
Patent number
US08779086B2

Reaction notes

Loading…