Triethylamine → 3-(3-fluoro-phenyl)-N-methoxy-N-methyl-acrylamide

HRID 857011Notes

Reaction equation

HRID 857011 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7](O)=[O:8].CCN=C=NCCC[N:21]([CH3:23])C.Cl.C(N(CC)CC)C.N[O:33][CH3:34].Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]([N:21]([O:33][CH3:34])[CH3:23])=[O:8])[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 886063-(3-Fluorophenyl)-2-propenoic acidHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 730107483-(3-fluoro-phenyl)-N-methoxy-N-methyl-acrylamideYield 96.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-fluorocinnamic acid (16.6 g), EDAC.HCl (23 g), DMAP (12.2 g), triethylamine (28 mL), and NH2OMe.HCl (12 g) in CH2Cl2 (300 mL) was stirred at room temperature for 16 h. The reaction was quenched with water, and the organic layer was washed with brine, dried over MgSO4 and filtered. The filtrated was evaporated in vacuo, and the crude product was purified by silica gel flash chromatography eluting with 33% hexanes in ethyl acetate gave the title compound (20.2 g) as a solid.

Workup

  1. customThe reaction was quenched with water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrated was evaporated in vacuo
  6. customthe crude product was purified by silica gel flash chromatography
  7. washeluting with 33% hexanes in ethyl acetate

Sources & evidence

ORD record
ord-c9cfd795b7584f9d9cdf34ef51abf70b
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

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