p-Toluidine → 3-Fluoro-2-methyl-2-(4-methylphenyl)aminopropionitrile

HRID 244990Notes

Reaction equation

HRID 244990 reaction equation
C[Si]([C:5]#[N:6])(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[F:15][CH2:16][C:17](=O)[CH3:18]>ClCCl>[F:15][CH2:16][C:17]([CH3:18])([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 9889FluoroacetoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 671345443-Fluoro-2-methyl-2-(4-methylphenyl)aminopropionitrileYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl cyanide (0.146 ml, 1.1 mmol) was added dropwise to the mixture of p-toluidine (0.107 g, 1 mmol) and fluoroacetone (0.082 g, 1.1 mmol). The reaction mixture was stirred at room temperature for 12 h and then concentrated under vacuum to obtain a brown liquid which was subjected to chromatography (dichloromethane) to yield 19a (0.179 g, 0.93 mmol, 93%) as a yellowish solid.

Workup

  1. concentrationconcentrated under vacuum
  2. customto obtain a brown liquid which

Sources & evidence

ORD record
ord-1d63cf68ccee4d4b8d6bcd1581ede352
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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