ChemicalBook CAS DataBase List N,N-DIETHYL-2-METHOXY-BENZAMIDE

N,N-DIETHYL-2-METHOXY-BENZAMIDE synthesis

10synthesis methods

Product Name:N,N-DIETHYL-2-METHOXY-BENZAMIDE
CAS Number:51674-10-3
Molecular formula:C12H17NO2
Molecular Weight:207.27

579-75-9 Synthesis

579-75-9
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$5.00/1g

109-89-7
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$10.00/5g

51674-10-3
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$53.20/250mg

Yield:51674-10-3 96.5%

Reaction Conditions:

Stage #1: 2-Methoxybenzoic acidwith oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at -10 - 20;
Stage #2: diethylamine in dichloromethane at 0 - 20; for 0.833333 h;

Steps:

4.2.8. N,N-Diethyl-2-methoxybenzamide (11)

To the solution of o-anisic acid (4.0 g, 26.3 mmol, 1 equiv) in dry CH₂Cl₂ was added DMF (1 mL, 13.2 mmol, 0.5 equiv) at room temperature to this oxalyl chloride (3.4 mL, 39.5 mmol, 1.5 equiv) was added at -10 °C drop wise over 10 min. Then reaction mixture was allowed to warm to room temperature and stirred at room temperature for 12 h Et₂NH (13.5 mL, 131.6 mmol, 5 equiv) was added to the reaction mixture at 0 °C over 20 min and the reaction mixture was stirred at 30 min at room temperature. The reaction mixture was concentrated under reduced pressure to give crude material, which was purified on column chromatography R_f 0.35 (hexane/EtOAc, 65:35) to give 11 (5.25 g, 96.5%) as yellowish oil; IR ν_max (Neat): 2978, 1627, 1431, 1243, 1018 cm^-1; ¹H NMR (300 MHz, CDCl₃+CCl₄): δ 7.32 (dt, J=1.7, 7.4 Hz, 1H), 7.19 (dd, J=1.7, 7.4 Hz, 1H), 6.96 (dt, J=0.8, 7.4 Hz, 1H), 6.90 (d, J=8.3 Hz, 1H), 3.81 (s, 3H), 3.59-3.55 (m, 2H), 3.14 (q, J=7.2 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H), 1.03 (t, J=7.2 Hz, 3H); ¹³C NMR (75 MHz, CDCl₃): δ 168.6, 155.1, 129.7, 127.3, 126.9, 120.6, 110.8, 55.4, 42.7, 38.7, 13.8, 12.8; ESIMS: m/z 230 [M+Na]⁺; HRESIMS: m/z 208.1342 [M+H]⁺ (calcd for C₁₂H₁₈NO₂: m/z 208.1337).