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

HRID 57245

Reaction equation

HRID 57245 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-bde749fce5c34878b571bc10872274f2
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Linked notes

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