Triethylamine → 4-Benzothiazol-2-YL-2-methyl-2H-pyrazol-3-ylamine

HRID 57292Notes

Reaction equation

HRID 57292 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](=[CH:13][N:14]([CH3:16])C)[C:11]#[N:12].C([N:19](CC)CC)C.S(O)(O)(=O)=O.CNN>CCO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[N:12][N:14]([CH3:16])[C:13]=1[NH2:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 165286Methylhydrazine sulfateHCID 51273352-Benzothiazol-2-yl-3-dimethylaminoacrylonitrile

Product 1

HCID 246913184-Benzothiazol-2-YL-2-methyl-2H-pyrazol-3-ylamineYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the 2-benzothiazol-2-yl-3-dimethylaminoacrylonitrile prepared above (96 mg, 0.42 mmol) and triethylamine (0.3 mL) in EtOH (10 mL) was treated with methylhydrazine sulfate (180 mg, 1.25 mmol) and the mixture was heated to reflux for 2 days. The solution was concentrated in vacuo and the residue was purified by flash chromatography (hexanes:EtOAc=1:1) to yield 47 mg (49%) of the title compound as a yellow powder. MS (m/z, ES+): 231 (M+1, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 days
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue was purified by flash chromatography (hexanes:EtOAc=1:1)

Sources & evidence

ORD record
ord-3aef9b3217984743b60618149830d0ee
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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