Formaldehyde → HCID 11817219, compound

HRID 719296Notes

Reaction equation

HRID 719296 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].[CH2:17]=O>C(O)C>[CH2:12]([N:14]([CH2:17][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][C:7]=1[OH:11])[CH2:15][CH3:16])[CH3:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 121243-Hydroxyacetanilide

Product 1

HCID 11817219HCID 11817219, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottomed flask containing 3-acetamidophenol (5 g) in ethanol (20 ml) was added diethylamine (2.6 g) and formaldehyde (1.1 g). The resulting mixture was stirred at reflux for 24 hours. After this time, the solvent was evaporated and the residue was purified by column chromatography (silica, dichloromethane/methanol 80:20) to give N-(4-Diethylaminomethyl-3-hydroxy-phenyl)-acetamide (4.1 g, 53%). 1H NMR (250 MHz, CDCl3) δH: 7.05 (1H, d, J=8.2), 6.89 (1H, d, J=8.2), 6.80 (1H, s), 3.70 (2H, s), 2.60 (2H, q, J=7.2), 2.12 (3H, s, NHCOCH3), 1.10 (3H, t, J=7.2). IR (NEAT) CM−1; 3500-2800 (broad-OH band), 1668, 1614, 1538, 1454, 1386, 1273, 1194, 1166, 1114, 1032, 863, 773 and 736.ACCURATE MASS: 237.16042 gmol−1 (C13H21O2N2 requires 237.16029); ELEMENTAL ANALYSIS; C, 64.07; H, 8.62; N, 10.88; (calc values; C, 65.67; H, 8.53; N, 11.86). MS; molecular ion peak at m/z=237

Workup

  1. temperatureat reflux for 24 hours
  2. customAfter this time, the solvent was evaporated
  3. customthe residue was purified by column chromatography (silica, dichloromethane/methanol 80:20)

Sources & evidence

ORD record
ord-356c79a37b354cc9b89ff080f2cd3509
Source dataset
uspto-grants-2006_11
Patent number
US07132431B2

Reaction notes

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