Hydrazine hydrate (1:1) → N-[2-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)ethyl]acetamide

HRID 57245

Reaktionsgleichung

Reaktionsgleichung von HRID 57245
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[C:13](SC)SC)[C:11]#[N:12].[C:18]([NH:21][CH2:22][CH2:23][NH2:24])(=[O:20])[CH3:19].O.[NH2:26][NH2:27]>C(O)C>[NH2:12][C:11]1[NH:27][N:26]=[C:13]([NH:24][CH2:23][CH2:22][NH:21][C:18](=[O:20])[CH3:19])[C:10]=1[C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Komponenten

5

Edukt 3

HCID 24654Hydrazine hydrate (1:1)HCID 66082N-(2-aminoethyl)acetamideHCID 28077272-Benzothiazol-2-yl-3,3-bis-methylsulfanylacrylonitrile

Produkt 1

HCID 66768089N-[2-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)ethyl]acetamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-benzothiazol-2-yl-3,3-bis-methylsulfanylacrylonitrile (200 mg, 0.74 mmol) and N-acetylethylenediamine (83 mg, 0.81 mmol) in ethanol (10 mL) was refluxed for 90 min. To this solution was added hydrazine hydrate (61 mg, 1.2 mmol), and the resulting mixture was refluxed overnight. Solids formed upon cooling. The resulting crystals were filtered and washed with ethanol to yield 150 mg (66%) of N-[2-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)ethyl]acetamide. MS (ES+): 317.1 (M+1, 100%).

Aufarbeitung

  1. temperaturewas refluxed for 90 min
  2. temperaturethe resulting mixture was refluxed overnight
  3. customSolids formed
  4. temperatureupon cooling
  5. filtrationThe resulting crystals were filtered
  6. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-bde749fce5c34878b571bc10872274f2
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434720B2

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