Bromobenzyl Cyanide → N-(4-amino-5-phenyl-thiazol-2-yl)-acetamide

HRID 874162

Reaktionsgleichung

Reaktionsgleichung von HRID 874162
Br[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]#[N:4].[C:11]([NH:14][C:15]([NH2:17])=[S:16])(=[O:13])[CH3:12]>C(O)C>[C:11]([NH:14][C:15]1[S:16][C:2]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[C:3]([NH2:4])[N:17]=1)(=[O:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 22044Bromobenzyl CyanideHCID 2723593Acetylthiourea

Produkt 1

HCID 85841531N-(4-amino-5-phenyl-thiazol-2-yl)-acetamideAusbeute 23,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

α-Bromophenylacetonitrile (1.08 g, 5.48 mmol) in ethanol (10 ml) was treated with N-acetylthiourea (649 mg, 5.49 mmol) at ambient temperature for 4 hr, and then heated to reflux for 3.5 hr. The cooled mixture was concentrated in vacuo and then partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 2-(acetylamino)-4-amino-5-phenylthiazole (295 mg, 23%).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 3.5 hr
  3. concentrationThe cooled mixture was concentrated in vacuo
  4. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ac4089a78c634ae690e094c6205119d1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980837B2

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