2,4,6-Trifluoroaniline → HCID 14995455, compound

HRID 2257176Notes

Reaction equation

HRID 2257176 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].[CH2:11]([C:20]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:11]([C:20]1([C:30]([NH:4][C:3]2[C:2]([F:1])=[CH:8][C:7]([F:9])=[CH:6][C:5]=2[F:10])=[O:31])[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 677652,4,6-TrifluoroanilineHCID 14995454HCID 14995454, compound

Product 1

HCID 14995455HCID 14995455, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1.0 g (6.8 mmole) 2,4,6-trifluoroaniline and 830 mg (6.8 mmole) 4-dimethylaminopyridine in 40 ml methylene chloride cooled to 5° C. under nitrogen was added a solution of 2.12 g (6.6 mmole) 2-n-nonyl-1,2,3,4-tetrahydro-2-naphthoyl chloride in 10 ml methylene chloride. The resulting solution was stirred at room temperature for 44 hours. Fifty milliters of methylene chloride was then added and the solution was washed sequentially with 30 ml aqueous hydrochloric acid, 30 ml water and 30 ml brine. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue (2.5 g) was purified by column chromatography on silica gel eluting with 2:1 methylene chloride-hexane to yield 1.66 g (58% yield) of the desired product as a white, low melting solid.

Workup

  1. washthe solution was washed sequentially with 30 ml aqueous hydrochloric acid, 30 ml water and 30 ml brine
  2. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness in vacuo
  4. customThe residue (2.5 g) was purified by column chromatography on silica gel eluting with 2:1 methylene chloride-hexane

Sources & evidence

ORD record
ord-3ac37939e9c74628b2648c3f1d34aff8
Source dataset
uspto-grants-1997_08
Patent number
US05656634

Reaction notes

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