Triethylamine → HCID 59277573, compound

HRID 2097005Notes

Reaction equation

HRID 2097005 reaction equation
[CH2:1]([O:3][C:4]1[C:12]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6]CN)[CH3:2].[C:18](Cl)(=[O:21])[CH:19]=[CH2:20].[CH2:23]([N:25](CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4]1[C:12]([O:13][C:14]([F:15])([F:16])[F:17])=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][N:25]([CH3:23])[C:18](=[O:21])[CH:19]=[CH2:20])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 66967533HCID 66967533, compound

Product 1

HCID 59277573HCID 59277573, compoundYield 118.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2-ethoxy-3-trifluoromethoxybenzyl)methylamine (0.720 g, 2.08 mmol) in CH2Cl2 (25 mL), was added acryloyl chloride (0.25 mL, 3.15 mmol) drop-wise. After stirring for five minutes, triethylamine (0.43 mL, 3.15 mmol) was added. The solution was allowed to stir under N2 for 3 h. The solution was diluted with CH2Cl2 (30 mL) and then washed with H2O (3×50 mL) and brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (0.746 g, 86%) as a yellow oil and as a mixture of amide rotamers: 1H NMR (500 MHz, CDCl3) δ 7.21-7.02 (m, 3H), 6.67-6.50 (m, 1H), 6.41-6.36 (m, 1H), 5.75-5.58 (m, 1H), 4.75-4.65 (m, 2H), 4.14-4.05 (m, 2H), 3.03-2.99 (m, 3H), 1.43-141 (m, 3H).

Workup

  1. stirringto stir under N2 for 3 h
  2. washwashed with H2O (3×50 mL) and brine (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eb63016b1e2b4563972a28b791efc98f
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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