2-Amino-5,5,6,6,6-pentafluorohexanenitrile → HCID 178470246, compound

HRID 2203387Notes

Reaction equation

HRID 2203387 reaction equation
[NH2:1][CH:2]([CH2:5][CH2:6][C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[C:3]#[N:4].F[B-](F)(F)F.[CH2:19]([O:21][C:22](=[O:27])[C:23](SC)=[NH2+:24])[CH3:20]>O1CCOCC1>[NH2:4][C:3]1[NH:24][C:23]([C:22]([O:21][CH2:19][CH3:20])=[O:27])=[N:1][C:2]=1[CH2:5][CH2:6][C:7]([F:12])([F:13])[C:8]([F:10])([F:9])[F:11]

Participants

4

Reactant 2

HCID 866790262-Amino-5,5,6,6,6-pentafluorohexanenitrileHCID 866790272-Ethoxy-1-(methylsulfanyl)-2-oxoethaniminium tetrafluoroborate

Product 1

HCID 178470246HCID 178470246, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-5,5,6,6,6-pentafluorohexanenitrile (0.5722 g, 2.83 mmol) and 2-ethoxy-1-(methylsulfanyl)-2-oxoethaniminium tetrafluoroborate (0.808 g, 3.45 mmol) in dry 1,4-dioxane (5.2 mL) was stirred at 25° C. under N2 for 6 days. The solution was concentrated in vacuo. The resulting residue was purified by silica gel chromatography using DCM/MeOH gradient to afford the desired product, as an orange oil. 1H NMR (500 MHz, CHCl3-d): δ 4.36 (q, J=7.1 Hz, 2H); 2.85 (br s, 2H); 2.41-2.16 (m, 3H); 2.11-1.94 (m, 1H); 1.35 (t, J=7.1 Hz, 3H). m/z 302.2 (M+H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-88954e9615454032b714897fcf1c92ee
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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