Ethyl bromopyruvate → Ethyl 2-cyclobutylthiazole-4-carboxylate

HRID 327568Notes

Reaction equation

HRID 327568 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-eddc81781e2944a5b902e1cac4c9313a
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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