alpha,alpha,alpha-Trifluoro-m-tolunitrile → HCID 12056690, compound

HRID 1057279Notes

Reaction equation

HRID 1057279 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[F:13][C:14]([F:28])([F:27])[C:15]([N:17]=[C:18]([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])=[O:16]>ClCCl>[F:13][C:14]([F:27])([F:28])[C:15]1[O:16][C:6]([C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=2)=[N:7][C:18]([C:23]([F:25])([F:26])[F:24])([C:19]([F:20])([F:22])[F:21])[N:17]=1

Participants

4

Reactant 2

HCID 67783alpha,alpha,alpha-Trifluoro-m-tolunitrileHCID 27607992,2,2-trifluoro-N-(1,1,1,3,3,3-hexafluoropropan-2-ylidene)acetamide

Product 1

HCID 12056690HCID 12056690, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Trifluoromethylbenzonitrile (5.8 g, 3.39 mmol) and 2,2,2-trifluoro-N-{2,2,2-trifluoro-1-(trifluoromethyl) ethylidene}acetamide (1.8 g, 6.90 mmol) were dissolved in dichloromethane (3 mL) and stirred in a sealed vial at room temperature for three days. The solvent and excess reagent were distilled off to give a colorless oil that was chromatographed on silica gel using 5 percent ethyl acetate/hexanes as eluent. The desired product was present as an oil (0.92 g, 63 percent yield) in the first eluted fraction. EIMS (m/z): 432 (M+), 413 (M−F), 363 (M-CF3).

Workup

  1. distillationThe solvent and excess reagent were distilled off
  2. customto give a colorless oil that
  3. customwas chromatographed on silica gel using 5 percent ethyl acetate/hexanes as eluent

Sources & evidence

ORD record
ord-bf66f9f17f07479b8df8cf22c624f6b0
Source dataset
uspto-grants-2003_02
Patent number
US06514911B1

Reaction notes

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