Triethylamine → 3-[2-(Methoxy-methylcarbamoyl)-vinyl]benzamide

HRID 841047Notes

Reaction equation

HRID 841047 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[CH3:11][O:12][N:13]([CH3:18])[C:14](=[O:17])[CH:15]=[CH2:16].C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][O:12][N:13]([CH3:18])[C:14]([CH:15]=[CH:16][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2024253-Iodobenzamide2×HCID 294174N-methoxy-N-methylprop-2-enamide

Product 1

HCID 541419803-[2-(Methoxy-methylcarbamoyl)-vinyl]benzamideYield 58%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

3-Iodo-benzamide compound 32 (3.0 g, 12.1 mmol), N-methoxy-N-methylacrylamide (Molander, G. G.; Stengel, P. J. Tetrahedron 1997, 53, 26, 8887-8912.) (1.8 g, 15 mmol), palladium (II) acetate (40 mg, 0.18 mmol), and triethylamine (2.1 mL, 15 mmol) were stirred in acetonitrile (12 mL) under argon in a sealed tube at 100° C. for 2.5 h. The reaction was allowed to cool, and solvent was removed. The residue was dissolved in CH2Cl2, washed with 0.1 N HCl and then with brine, dried (MgSO4), and concentrated. Recrystallization twice from methanol gave 1.64 g (58%) of 3-[2-(methoxy-methylcarbamoyl)-vinyl]benzamide 43 as a white solid. 1H NMR (CDCl3) δ 8.06 (1 H, s), 7.78 (1 H, d, J=7.8 Hz), 7.73 (1 H, d, J=16.2 Hz), 7.69 (1 H, d, J=7.8 Hz), 7.46 (1 H, t, J 7.8 Hz), 7.10 (1 H, d, J=16.2 Hz), 6.33 (1 H, br s), 5.97 (1 H, br s), 3.77 (3 H, s), 3.31 (3 H, s); IR (KBr) 3385, 3173, 1680, 1649, 1613, 1582, 1476, 1433, 1397, 1182, 1105 cm−1. Anal. (C12H14N2O3.0.33 H2O) C, H, N.

Workup

  1. temperatureto cool
  2. customsolvent was removed
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with 0.1 N HCl
  5. dry with materialwith brine, dried (MgSO4)
  6. concentrationconcentrated
  7. customRecrystallization twice from methanol

Sources & evidence

ORD record
ord-67dd04c127ab4b6cb7a43a492bfe1c21
Source dataset
uspto-grants-2002_04
Patent number
US06369226B1

Reaction notes

Loading…