Triethylamine → HCID 86673913, compound

HRID 1887477Notes

Reaction equation

HRID 1887477 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH2:6]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[CH2:7][CH:8]=[CH2:9].CCN(CC)CC>>[CH2:6]([N:10]([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][CH:12]=1)[C:1](=[O:4])[CH:2]=[CH2:3])[CH2:7][CH:8]=[CH2:9]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 64315559HCID 64315559, compound

Product 1

HCID 86673913HCID 86673913, compoundYield 54%

Procedure

Acryloyl chloride (0.7 g, 7.8 mmol) was added dropwise to a solution of But-3-enyl-(4-trifluoromethoxy-phenyl)-amine (1.2 g, 5.2 mmol) and Et3N (1.1 g, 10.4 mmol). The mixture was stirred at ambient temperature overnight. The mixture was extracted with DCM, washed with brine, dried over anhydrous Na2SO4. The solvent was removed by reduced pressure and the residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=10/1) to give N-But-3-enyl-N-(4-trifluoromethoxy-phenyl)-acrylamide (0.8 g, 54%). 1H NMR (300 MHz, CDCl3): δ 7.35-7.18 (m, 4H), 6.38-6.35 (m, 1H), 5.96-5.93 (m, 1H), 5.78-5.74 (m, 1H), 5.68-5.64 (m, 1H), 5.08-5.01 (m, 2H), 3.84 (t, 2H, J=7.5 Hz), 2.31-2.27 (m, 2H). LC-MS: [M+1]+ 286.1.

Workup

  1. extractionThe mixture was extracted with DCM
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed by reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-f28dd07c6d8448588a5e13284770a750
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

Loading…