Acetone → HCID 6110721, compound

HRID 705461Notes

Reaction equation

HRID 705461 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:13][C:14]([CH3:16])=[O:15].[OH-:17].[Na+]>CCO>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[CH:13]/[C:14](=[O:15])/[CH:16]=[CH:9]/[C:8]2[CH:11]=[CH:12][C:5]([NH:4][C:1](=[O:17])[CH3:2])=[CH:6][CH:7]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 739424-Acetamidobenzaldehyde

Product 1

HCID 6110721HCID 6110721, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of p-acetamidobenzaldehyde (8.15 g, 50 mmol) dissolved in 200 mL of hot EtOH) and acetone (1.8 mL, 25 mmol) was added dropwise to a solution of aq. NaOH solution (2 N, 25 mL) in EtOH (150 mL). The reaction mixture was stirred for 4 h at ambient temperature and the resulting orange precipitate was filtered, washed with water and dried in vacuo to afford NW270 as a bright yellow solid (4.6 g, 53%). mp: 253-255° C. 1H NMR (250 MHz, DMSO-d6) δ (ppm): 10.18 (s, 2H, NH), 7.81-7.58 (m, 10H, HAr, Hvin), 7.22 (d, 3J=16.0 Hz, 2H, Hvin), 2.08 (s, 6H, CH3). 13C NMR (75 MHz, DMSO-d6) δ (ppm): 188.2 (C), 168.6 (C), 142.1 (CH), 141.4 (C), 129.4 (CH), 124.1 (CH), 118.9 (CH), 24.1 (CH3). MS (EI) m/z: 348.2 (M+). Anal. calcd for C21H20N2O3: C, 72.40; H, 5.79; N, 8.04. Found: C, 72.14; H, 5.78; N, 7.97%.

Workup

  1. filtrationthe resulting orange precipitate was filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b9ab65d834284d4d88418df2209c0d26
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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