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

HRID 972831Notes

Reaction equation

HRID 972831 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>N1CCCCC1.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 8082PiperidineCatalystHCID 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 piperidine was heated at 100°-100°C for 5 hours and was then returned to room temperature and poured into 500 ml of water. The pH of the solution was adjusted to 3 by addition of N sulfuric acid and the mixture was vacuum filtered. The recovered precipitate was dried to obtain 27.8 g of 3-(2-methyl-5-thiazolyl)-2-propenoic acid which was crystallized from 800 ml of ethanol containing 10% ethanol to obtain 23.8 of the said product melting at 204°C.

Workup

  1. temperaturewas heated at 100°-100°C for 5 hours
  2. customwas then returned to room temperature
  3. filtrationfiltered
  4. customThe recovered precipitate was dried

Sources & evidence

ORD record
ord-40680e7096e6407bb86848c195765d51
Source dataset
uspto-grants-1977_10
Patent number
US04053618

Reaction notes

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