Ethyl 2-chloroacetoacetate → Ethyl 2-anilino-4-methyl-1,3-thiazole-5-carboxylate

HRID 917388

Reaktionsgleichung

Reaktionsgleichung von HRID 917388
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH:12]([C:18](=O)[CH3:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH3:19][C:18]1[N:10]=[C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:9][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

4

Edukt 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 676454Phenylthiourea

Produkt 1

HCID 807772Ethyl 2-anilino-4-methyl-1,3-thiazole-5-carboxylateAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 70 ml of ethanol, 10.7 g (70 mmol) of phenylthiourea and 11.6 g (70 mmol) of ethyl 2-chloro-3-oxobutanate were dissolved, followed by heating under refluxing for 8 hours. The reaction liquid was concentrated and dissolved in ethyl acetate and the organic layer was washed with an aqueous solution of sodium carbonate, water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentrating under reduced pressure. Solid obtained was washed with diisopropyl ether to obtain 16.8 g (yield: 91%) of ethyl 4-methyl-2-(N-phenylamino)thiazole-5-carboxylate. (2) To 50 ml of ethanol, 12.8 g (49 mmol) of ethyl-4-methyl-2-(N-phenylamino)thiazole-5-carboxylate was dissolved, followed by adding 24 g (150 mmol) of 25% sodium hydroxide aqueous solution, and stirring at 80° C. for 15 hours. The reaction liquid was poured into ice water, and acetic acid was added to make acidic. Crystal precipitated was filtered, washed with water and a mixed solvent of hexane/ethyl acetate and dried to obtain 5.50 g (yield: 48%) of 4-methyl-2-(N-phenylamino)thiazole-5-carboxylic acid.

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder refluxing for 8 hours
  3. customThe reaction liquid
  4. concentrationwas concentrated
  5. dissolutiondissolved in ethyl acetate
  6. washthe organic layer was washed with an aqueous solution of sodium carbonate, water
  7. dry with materialby drying over anhydrous magnesium sulfate
  8. concentrationconcentrating under reduced pressure
  9. customSolid obtained
  10. washwas washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6f9ad1ae7dd8467e9631e333a8a5a164
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273878B2

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