Sodium Hydroxide → 2-Cyclopropylmethylthio-4-(5-trifluoromethylpyridin-2-yl)benzonitrile

HRID 1432746Notes

Reaction equation

HRID 1432746 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11](F)[CH:10]=2)=[N:7][CH:8]=1.Br.[CH:21]1([CH2:24][S:25]C(=N)N)[CH2:23][CH2:22]1.[OH-].[Na+]>CN(C)C=O>[CH:21]1([CH2:24][S:25][C:11]2[CH:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:8][N:7]=3)[CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2777025[(Cyclopropylmethyl)sulfanyl]methanimidamide hydrobromideHCID 22170891HCID 22170891, compound

Product 1

HCID 221708942-Cyclopropylmethylthio-4-(5-trifluoromethylpyridin-2-yl)benzonitrileYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.8 g (6.8 mmol) of 4-(5-trifluoromethylpyridin-2-yl)-2-fluorobenzonitrile, 1.6 g (7.6 mmol) of S-cyclopropylmethylisothiourea hydrobromide salt and 50 ml of N,N-dimethylformamide were put into a round-bottomed flask and stirred together with 1.6 g (8 mmol) of 20% aqueous sodium hydroxide overnight. The solvent was distilled off under reduced pressure, and the reaction mixture was separated with 50 ml of water and 50 ml of ethyl acetate. The organic layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.2 g of 2-cyclopropylmethylthio-4-(5-trifluoromethylpyridin-2-yl)benzonitrile (yield 96%) as pale yellow feathery crystals (m.p. 135-136° C.).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe reaction mixture was separated with 50 ml of water and 50 ml of ethyl acetate
  3. washThe organic layer was washed with 50 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0e4f63954d5b4206bbd92eac1ce1316c
Source dataset
uspto-grants-2009_11
Patent number
US07612105B2

Reaction notes

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