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

HRID 1959852Notes

Reaction equation

HRID 1959852 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-fc0918b3fe9c4efca19694caf4735407
Source dataset
uspto-grants-2013_04
Patent number
US08410272B2

Reaction notes

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