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

HRID 498950Notes

Reaction equation

HRID 498950 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-368dedc3865c421d81d4a818cf4af432
Source dataset
uspto-grants-2010_08
Patent number
US07767626B2

Reaction notes

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