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

HRID 407351Notes

Reaction equation

HRID 407351 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-bc864d6cfc2d496c849d58d1cc778dee
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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