Pyridine → 2-(Trimethylacetamido)-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole

HRID 261750

Reaktionsgleichung

Reaktionsgleichung von HRID 261750
Br[CH2:2][C:3](=O)[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:6].N1C=CC=CC=1.[CH3:25][C:26]([CH3:34])([CH3:33])[C:27]([NH:29][C:30]([NH2:32])=[S:31])=[O:28]>O.C(O)C>[CH3:25][C:26]([CH3:34])([CH3:33])[C:27]([NH:29][C:30]1[S:31][CH:2]=[C:3]([CH2:4][C:5](=[O:6])[NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:32]=1)=[O:28]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 18948826N-trimethylacetylthioureaHCID 223476964-Bromo-3'-trifluoromethylacetoacetanilide

Produkt 1

HCID 273974612-(Trimethylacetamido)-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazoleAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A 500 ml reaction flask fitted with a magnetic stirrer, heating mantle, thermometer and water-cooled condenser was charged with 44.7 g (0.138 mole) of 4-bromo-3'-trifluoromethylacetoacetanilide, 350 ml of absolute ethanol and 15 g (0.19 mole) of pyridine. A 26 g - sample (0.162 mole) of N-trimethylacetylthiourea [m.p. 140°-42°; prepared as described by Moore and Crossley in The Journal of the American Chemical Society, vol. 62, p. 3273 (1940)] was added to the reaction solution. As the substituted thiourea dissolved, the reaction temperature increased from 24° to 31°. The solution was refluxed for four hours and poured into 1.5 liters of water. With stirring, the residual oil crystallized. The product was collected and washed with water. There was obtained 46.8 g (88%) of white solid, m.p. 147°-52°. One recrystallization from ethyl acetate - heptane yielded material which melted at 153°-55°. N.M.R. (dimethyl-d 6 sulfoxide) ∂ 1.3 (tert-butyl), 3.8 (CH2), 6.9 (hetero-aromatic), 7.3-8.1 (aromatic).

Aufarbeitung

  1. customA 500 ml reaction flask
  2. customfitted with a magnetic stirrer
  3. temperatureheating mantle
  4. customprepared
  5. addition3273 (1940)] was added to the reaction solution
  6. temperaturethe reaction temperature increased from 24° to 31°
  7. temperatureThe solution was refluxed for four hours
  8. customthe residual oil crystallized
  9. customThe product was collected
  10. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-54cb37179b7041a6a28872eb34f89f87
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152329

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