Malonic Acid → 3-(2-Methyl-5-thiazolyl)-2-propenoic acid

HRID 437941Notes

Reaction equation

HRID 437941 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH:7]=O)=[CH:5][N:6]=1.N1C=CC=CC=1.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].S(=O)(=O)(O)O>N1C=CC=CC=1.O>[CH3:1][C:2]1[S:3][C:4]([CH:7]=[CH:16][C:17]([OH:19])=[O:18])=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 867Malonic AcidHCID 1049PyridineHCID 1118Sulfuric AcidHCID 139347282-Methyl-1,3-thiazole-5-carbaldehyde

Product 1

HCID 541284263-(2-Methyl-5-thiazolyl)-2-propenoic acidYield 72%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 29 g of 2-methyl-5-thiazolecarboxaldehyde, 30 ml of pyridine, 29 g of malonic acid and 30 drops of pyridine was heated at 100°-110° C. for 5 hours and after cooling to room temperature, the mixture was poured into 500 ml of water. The pH of the solution was adjusted to 3 by addition of N sulfuric acid and the precipitate formed was recovered by vacuum filtration and was dried to obtain 27.8 g of 3-(2-methyl-5-thiazolyl)-2-propenoic acid which were crystallized from 10% aqueous ethanol to obtain 23.8 g of the said product melting at 204° C.

Workup

  1. temperaturewas heated at 100°-110° C. for 5 hours
  2. customthe precipitate formed
  3. filtrationwas recovered by vacuum filtration
  4. customwas dried

Sources & evidence

ORD record
ord-c233c545d5f2409699e10244a3d1cd5c
Source dataset
uspto-grants-1977_06
Patent number
US04032643

Reaction notes

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