Ethyl bromopyruvate → Ethyl 2-cyclobutylthiazole-4-carboxylate

HRID 1609330Notes

Reaction equation

HRID 1609330 reaction equation
[CH:1]1([C:5](=[S:7])[NH2:6])[CH2:4][CH2:3][CH2:2]1.Br[CH2:9][C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:14]([O:13][C:11]([C:10]1[N:6]=[C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)[S:7][CH:9]=1)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 22141088Cyclobutanecarbothioamide

Product 1

HCID 54513950Ethyl 2-cyclobutylthiazole-4-carboxylateYield 39.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture composed of 9.7 g of cyclobutancarbothioamide, 16.5 g of ethyl bromopyruvate and 200 ml of ethyl alcohol was heated to reflux for 1 hr. The reaction mixture was partially condensed in vacuo and the residual materials were diluted with ice water and and excess of saturated sodium bicarbonate solution. The solids were collected to yield 7.0 g of 2-cyclobutyl-4-thiazolecarboxylic acid ethyl ester; m.p. 48°-50° C. after recrystallization from pentane.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hr
  3. customcondensed in vacuo
  4. customThe solids were collected

Sources & evidence

ORD record
ord-df771a0a379b406ea2b9b346b05952b7
Source dataset
uspto-grants-1995_03
Patent number
US05399702

Reaction notes

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