Phenacyl bromide → N~1~-(4-Phenyl-1,3-thiazol-2-yl)benzene-1,3-diamine

HRID 2086775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2086775
C([NH:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH2:14])=[S:13])[CH:8]=[CH:9][CH:10]=1)(=O)C.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O>C(O)C>[C:19]1([C:17]2[N:14]=[C:12]([NH:11][C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[NH2:4])[S:13][CH:16]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 6259Phenacyl bromideHCID 6451295Acetamide, N-(3-((aminothioxomethyl)amino)phenyl)-

Produkt 1

HCID 22724394N~1~-(4-Phenyl-1,3-thiazol-2-yl)benzene-1,3-diamineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of N-(3-acetylaminophenyl)thiourea (0.84 g) and 2-bromoacetophenone (0.84 g) in ethanol (10 ml) was refluxed for 15 minutes. After evaporation of the solvent, 3N hydrochloric acid was added thereto and the mixture was refluxed for 30 minutes. The mixture was made basic with sodium bicarbonate and extracted with ethyl acetate. The organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was crystallized from ethanol to give 3-(4-phenylthiazol-2-yl)aminoaniline (0.88 g).

Aufarbeitung

  1. temperaturewas refluxed for 15 minutes
  2. customAfter evaporation of the solvent, 3N hydrochloric acid
  3. additionwas added
  4. temperaturethe mixture was refluxed for 30 minutes
  5. extractionextracted with ethyl acetate
  6. washThe organic solution was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6cd90584d27645e1bf2ef90a9cd72202
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727245B2

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