Malonic Acid → 2-Thiazoleacrylic acid

HRID 915662Notes

Reaction equation

HRID 915662 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[CH:6][N:7]=1)=O.C(O)(=O)[CH2:9][C:10]([OH:12])=[O:11]>N1C=CC=CC=1.N1CCCCC1.O>[S:4]1[CH:5]=[CH:6][N:7]=[C:3]1[CH:1]=[CH:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 2

HCID 867Malonic AcidHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 534018492-Thiazoleacrylic acidYield 12.4%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Mix 2-formyl thiazole (10.0 g, 88.4 mmol) and malonic acid (9.2 g, 88.4 mmol). Dissolve in pyridine (7.2 mL, 88.5 g) and add 3 drops of piperidine. Heat the mixture at 100° C. under nitrogen for 3 hours, cool, dilute with water, and filter the solids to afford 1.7 g of the title compound as a white solid. Concentrate the filtrate, acidify with 1N HCl, extract with ethyl acetate (2×100 mL), wash with brine (100 mL), dry (sodium sulfate), filter and concentrate to afford an additional 4.8 g of 3-thiazol-2-yl-acrylic acid MS: m/e=156 (MH+).

Workup

  1. temperaturecool
  2. filtrationfilter the solids

Sources & evidence

ORD record
ord-4ad494d41c66427c9125b8276f419fc5
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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