Triethylamine → HCID 102287610, compound

HRID 1478811Notes

Reaction equation

HRID 1478811 reaction equation
[CH2:1]([C:4]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=1[NH2:6])[CH:2]=[CH2:3].CCN(CC)CC.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25]>C1COCC1>[CH2:1]([C:4]1[CH:10]=[C:9]([O:11][C:12]([F:13])([F:14])[F:15])[CH:8]=[CH:7][C:5]=1[NH:6][C:23](=[O:26])[CH:24]=[CH2:25])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 118513273HCID 118513273, compound

Product 1

HCID 102287610HCID 102287610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-allyl-4-(trifluoromethoxy)aniline (17.5 g, 80.6 mmol) in THF (1000 ml), cooled in a dry ice bath to a temperature below −10° C. was added Et3N (8.96 g, 17.3 mmol) and acryloyl chloride (7.98 g, 88.7 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 hr. The resulting mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with water and brine. The organic portion was dried over Na2SO4, filtered and concentrated in under reduced pressure to give a white solid which was washed with ethyl acetate to give the title compound.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in under reduced pressure
  7. customto give a white solid which
  8. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-e283f2b96d4f44fab1f529f8633d90c9
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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