Triethylamine → HCID 86673915, compound

HRID 1887484Notes

Reaction equation

HRID 1887484 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].CCN(CC)CC.[C:25](Cl)(=[O:28])[CH:26]=[CH2:27]>C(Cl)Cl>[CH2:1]([N:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([F:15])([F:16])[F:17])=[CH:8][CH:7]=1)[C:25](=[O:28])[CH:26]=[CH2:27])[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 86673914HCID 86673914, compound

Product 1

HCID 86673915HCID 86673915, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of but-3-enyl-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-amine (1.56 g, 6 mmol) and NEt3 (1.7 g, 17 mmol) in 30 mL of DCM, acryloyl chloride (0.65 g, 7 mmol) was added slowly into at 0° C. The mixture was stirred at ambient temperature overnight. And then the solution was washed with water (2×15 mL) and brine (2×20 mL), dried with anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate=20:1) to obtain the title compound (1.6 g, 89%) as colorless oil. LC-MS: 300.1 [M+1]+.

Workup

  1. additionwas added slowly into at 0° C
  2. washAnd then the solution was washed with water (2×15 mL) and brine (2×20 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record
ord-f5c6e145282a46e4bc2aa34c9f0e60e6
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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