Dimethylformamide → N-(2-naphtyl)methyl 3-(2-aminophenyl)-2-methyl-2-propenamide

HRID 1976902Notes

Reaction equation

HRID 1976902 reaction equation
CN(C)C=O.[CH2:6]([NH:14][C:15](=[O:30])[C:16]([CH3:29])=[CH:17][C:18]1[CH:23]=[C:22](OC)[C:21](OC)=[CH:20][C:19]=1[NH2:28])CC1C=CC=CC=1.[N+](C1C=CC(OC(=O)C(C)=CC2C=CC=CC=2N)=CC=1)([O-])=O.[CH:53]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:56]=[CH:55][C:54]=1N>C(Cl)Cl.CO.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH:53]1[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:56]=[CH:55][C:54]=1[CH2:6][NH:14][C:15](=[O:30])[C:16]([CH3:29])=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:28]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 70572-NaphthylamineHCID 702148893-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid phenethyl amideHCID 702154653-(2-Aminophenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester

Product 1

HCID 70230097N-(2-naphtyl)methyl 3-(2-aminophenyl)-2-methyl-2-propenamideYield 199.7%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

Into 4 ml of dimethylformamide, 0.65 g (2.2 mmol) of (E) 3-(2-aminophenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester and 0.69 g (4.4 mmol) of 2-naphtylamine (manufactured by Aldrich Chemical Co., Inc.) were dissolved; and, with 0.36 ml of triethylamine (manufactured by Wako Pure Chemical Industries, Ltd.) being added thereto, the mixture was reacted at room temperature for 20 hours. After the completion of the reaction was verified by TLC, ethyl acetate and water were added to the mixture. The resulting ethyl acetate layer was fractionated, and was washed several times with a 5% aqueous sodium hydrogencarbonate solution and then with a saturated aqueous sodium chloride solution. After the washed solution was dried with magnesium sulfate anhydride, the solvent was evaporated under a reduced pressure, whereby a crude product was obtained. This product was refined by a silica gel column chromatography (developing solvent: methylene chloride/methanol=95/5), whereby 1.39 g of the aimed compound were obtained (yield: quantitative).

Workup

  1. customthe mixture was reacted at room temperature for 20 hours
  2. additionwere added to the mixture
  3. washwas washed several times with a 5% aqueous sodium hydrogencarbonate solution
  4. dry with materialAfter the washed solution was dried with magnesium sulfate anhydride
  5. customthe solvent was evaporated under a reduced pressure, whereby a crude product
  6. customwas obtained

Sources & evidence

ORD record
ord-1c16ed3f30c54c19b09f4f369e6be6d9
Source dataset
uspto-grants-2001_05
Patent number
US06229020B1

Reaction notes

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