Water → HCID 18931461, compound

HRID 1598972Notes

Reaction equation

HRID 1598972 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][C:25]([CH3:30])=[CH:26][C:27](Cl)=[O:28].O>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:27](=[O:28])[CH:26]=[C:25]([CH3:30])[CH3:24])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1023943-Methyl-2-butenoyl chlorideHCID 11954849Benzenamine, 3-methoxy-N-(4-methylphenyl)-2×

Product 1

HCID 18931461HCID 18931461, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.10 g (0.47 mmol) of N-(4-methylphenyl)-3-methoxyaniline (Compound 15) in 3.0 mL of tetrahydrofuran stirring at 0° C. under argon, were added 0.15 mL (0.11 g, 1.1 mmol) of triethylamine and then 0.19 g (1.6 mmol) of 3,3-dimethylacryloyl chloride. The reaction mixture was allowed to warm to room temperature over 30 minutes and then heated at 50° C. for 13 hours. The reaction mixture was cooled, water was added, and the mixture was extracted with diethyl ether (2x). The combined organic layers were then washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give an oil. The mixture was purified by flash chromatography (10% ethyl acetate in hexanes, 20% ethyl acetate in hexanes) to give the title compound as a yellow oil. PNMR (300 MHz, CDCl3) d 1.75 (3 H, s), 2.16 (3 H, s), 2.34 (3 H, s), 3.76 (3 H, s), 5.61 (1 H, s), 6.75-6.81 (2 H, m), 7.08 (2 H, d, J=8.5 Hz), 7.14 (2 H, d, J=8.5 Hz), 7.23 (1 H, t, J=7.8 Hz).

Workup

  1. temperatureheated at 50° C. for 13 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe mixture was extracted with diethyl ether (2x)
  4. washThe combined organic layers were then washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an oil
  9. customThe mixture was purified by flash chromatography (10% ethyl acetate in hexanes, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cc45fc9cda1e48f4896e6de496cf77e4
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

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