Ethyl benzoylacetate → HCID 59520403, compound

HRID 1162519Notes

Reaction equation

HRID 1162519 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH2:7].[C:13]([CH2:21][C:22](OCC)=[O:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][NH:7][C:22](=[O:23])[CH2:21][C:13](=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 1508972-(2,4-Dichlorophenoxy)ethylamine

Product 1

HCID 59520403HCID 59520403, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 2-(2,4-Dichloro-phenoxy)-ethylamine 29 (412 mg, 2.0 mmol) in toluene (1.5 mL) is added ethyl benzoylacetate 34 (384 mg, 2.0 mmol). The mixture is heated to 160° C. for 10 minutes in a microwave. The resulting mixture is concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford N-[2-(2,4-dichloro-phenoxy)-ethyl]-3-oxo-3-phenyl-propionamide 35 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=7.98 (d, J=7.2 Hz, 2H), 7.60-7.35 (m, 5H), 7.15 (dd, J=2.5 Hz, J=8.8 Hz, 1H), 6.83 (d, J=8.8 Hz, 1H), 4.10 (t, J=5.2 Hz, 2H), 3.98 (s, 2H), 3.76 (q, J=5.3 Hz, 2H). MS calculated for C17H16Cl2NO3 (M+H+) 352.0, found 352.1.

Workup

  1. concentrationThe resulting mixture is concentrated
  2. custompurified on reverse phase HPLC (H2O/MeCN gradient)

Sources & evidence

ORD record
ord-4a59420966784bf3a3d1132f50fe727a
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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