Magnesium Carbonate → Ethyl 2-propylthiazole-5-carboxylate

HRID 1659120Notes

Reaction equation

HRID 1659120 reaction equation
[C:1]([NH2:6])(=[S:5])[CH2:2][CH2:3][CH3:4].[CH:7]([CH:9](Cl)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O.C(=O)([O-])[O-].[Mg+2]>O1CCOCC1>[CH2:2]([C:1]1[S:5][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][N:6]=1)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11029Magnesium CarbonateHCID 118030Ethyl (chloroformyl)acetateHCID 12454243Butanethioamide

Product 1

HCID 21413783Ethyl 2-propylthiazole-5-carboxylateYield 79.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 38 g of thiobutyramide, 54.2 g of ethyl 2-formyl-2-chloro-acetate, 185 ml of dioxane and 22 g of magnesium carbonate was heated for 4 hours at 60°C and the precipitate formed was removed by filtration. The dioxane was distilled from the filtrate and the residue was taken up in 665 ml of a 1-1 ethyl ether-water mixture. The ether phase was recovered by decantation and was washed with aqueous 10% hydrochloric acid solution and then with water until the wash waters were neutral, dried over magnesium sulfate and distilled to dryness. The residue was distilled to obtain 57 g of ethyl 2-n-propylthiazol-5-carboxylate boiling at 95°-106°C under 0.5 mm Hg.

Workup

  1. customthe precipitate formed
  2. customwas removed by filtration
  3. distillationThe dioxane was distilled from the filtrate
  4. customThe ether phase was recovered by decantation
  5. washwas washed with aqueous 10% hydrochloric acid solution
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled to dryness
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-5de2a2621d6d43db9fa6194c20c4e9d3
Source dataset
uspto-grants-1976_06
Patent number
US03966950

Reaction notes

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