Ammonium Hydroxide → 1-ethyl-5-(2-methanesulfonylethyl)-1H-pyrazole-3-carbonitrile

HRID 1984345Notes

Reaction equation

HRID 1984345 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:5]([C:14]([NH2:16])=O)=[N:4]1)[CH3:2].[OH-].[NH4+]>P(Cl)(Cl)(Cl)=O>[CH2:1]([N:3]1[C:7]([CH2:8][CH2:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:5]([C:14]#[N:16])=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 66958625HCID 66958625, compound

Product 1

HCID 669591691-ethyl-5-(2-methanesulfonylethyl)-1H-pyrazole-3-carbonitrileYield 96.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A modification of the method described in Part E of Examples 1-4 was used to treat 1-ethyl-5-(2-methanesulfonylethyl)-1H-pyrazole-3-carboxamide (3.46 g, 14.1 mmol) with phosphorous oxychloride (10 mL). The reaction was heated for 2.5 hours. After the addition of ammonium hydroxide (35 mL of 28%) a precipitate formed. The mixture was stirred for 30 minutes, and the precipitate was isolated by filtration and washed with water to provide 3.1 g of 1-ethyl-5-(2-methanesulfonylethyl)-1H-pyrazole-3-carbonitrile as a white powder.

Workup

  1. temperatureThe reaction was heated for 2.5 hours
  2. customformed
  3. customthe precipitate was isolated by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-b5d1c2a05a794dc6aeb51b2ea9049353
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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