Water → 2-Amino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole

HRID 261751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 261751
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].[NH2:19][C:20]([NH2:22])=[S:21].O>C(O)C>[NH2:22][C:20]1[S:21][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:19]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 2723790Thiourea2×HCID 223476964-Bromo-3'-trifluoromethylacetoacetanilide

Produkt 1

HCID 213211472-Amino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazoleAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 31.1 g (0.096 mole) of 4-bromo-3'-trifluoromethylacetoacetanilide in 130 ml of absolute ethanol was carefully mixed with 8.4 g (0.11 mole) of thiourea. As the thiourea dissolved, the temperature of the solution increased from 23° to 38°. After the exothermic reaction had subsided, the solution was refluxed for four hours and poured into 130 ml of water. A small quantity of insoluble material was removed by filtration and the filtrate was made basic (pH 9) with ammonium hydroxide. Stirring and cooling yielded a crystalline solid which was collected. There was obtained 19 g (65.7%) of dry product, m.p. 116°-18°. N.M.R. (dimethyl-d6 sulfoxide) ∂ 3.4 (CH2), 6.3 (hetero-aromatic), 6.8 (NH2), 7.3-8.0 (aromatic), 10.3 (HNC=0).

Aufarbeitung

  1. temperaturethe temperature of the solution increased from 23° to 38°
  2. customAfter the exothermic reaction
  3. temperaturethe solution was refluxed for four hours
  4. customA small quantity of insoluble material was removed by filtration
  5. temperaturecooling
  6. customyielded a crystalline solid which
  7. customwas collected

Quellen und Nachweise

ORD-Eintrag
ord-e0fad6db95a442a1ad570b234bcdbdca
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152329

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