ChemicalBook CAS DataBase List 2-CYANO-N-(2,4-DICHLORO-5-METHOXYPHENYL) ACETAMIDE

2-CYANO-N-(2,4-DICHLORO-5-METHOXYPHENYL) ACETAMIDE synthesis

4synthesis methods

Product Name:2-CYANO-N-(2,4-DICHLORO-5-METHOXYPHENYL) ACETAMIDE
CAS Number:846023-24-3
Molecular formula:C10H8Cl2N2O2
Molecular Weight:259.09

98446-49-2

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846023-24-3

Example 4 Synthesis of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide: 2,4-dichloro-5-methoxyaniline (5.00 g, 26 mmol) was mixed with cyanoacetic acid (2.28 g, 26.8 mmol) at 50 °C. Tetrahydrofuran was added to the mixture until complete dissolution. Subsequently, the solution was heated to reflux and 1,3-diisopropylcarbodiimide (4.2 mL, 26.8 mmol) was added slowly and dropwise. After 30 minutes of reaction, the reaction mixture was cooled to about 15 °C in an ice bath. The solid product formed was collected by filtration and washed with tetrahydrofuran. The filtrate was slowly poured into water and stirred for 30 minutes. The white solid product was collected by filtration again, washed with water and dissolved in 500 mL of ethyl acetate. The resulting solution was dried over anhydrous sodium sulfate and subsequently concentrated under vacuum to afford 5.9 g (88% yield) of the target compound 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide as a white solid with a melting point of 180-181 °C.1H NMR (400 MHz, DMSO-d6) δ 3.84 (s, 3H), 4.02 (s, 2H) 7.58 (s, 1H), 7.66 (s, 1H), 10.00 (s, 1H); mass spectra (electrospray ionization) m/z 257.0, 259.0 ([M-H]-). Elemental analysis (C10H8Cl2N2O2) calculated values: C, 46.36; H, 3.11; N, 10.81. measured values: C, 46.25; H, 3.10; N, 10.85.

98446-49-2 Synthesis

98446-49-2
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372-09-8
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846023-24-3
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Yield:846023-24-3 88%

Reaction Conditions:

with diisopropyl-carbodiimide in tetrahydrofuran; for 0.5 h;Product distribution / selectivity;Heating / reflux;

Steps:

4 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

EXAMPLE 4 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide 2,4-Dichloro-5-methoxyaniline (5.00 g, 26 mmol) and cyanoacetic acid (2.28 g, 26.8 mmol) were mixed in 50 mL of tetrahydrofuran until a solution formed. This solution was heated to reflux and 1,3-diisopropylcarbodiimide (4.2 mL, 26.8 mmol) was added dropwise. After 30 minutes the mixture was cooled to ~15° C. in an ice-bath. The solid was collected by filtration and washed with tetrahydrofuran. The filtrate was slowly poured into water and stirred for 30 minutes. The white solid was collected by filtration, washed with water, and was then dissolved in 500 mL of ethyl acetate. The solution was dried over sodium sulfate and concentrated in vacuo to give 5.9 g (88%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide as a white solid, mp 180-181° C.; ¹H NMR (400 MHz, DMSO-d₆) δ 3.84 (s, 3H), 4.02 (s, 2H), 7.58 (s, 1 H), 7.66 (s, 1 H), 10.00 (s, 1 H); MS (ES) m/z257.0, 259.0 (M-H)- Analysis for C₁₀H₈Cl₂N₂O₂; Calcd: C, 46.36; H, 3.11; N, 10.81. Found: C, 46.25; H, 3.10; N, 10.85.

References:

US2005/43537,2005,A1 Location in patent:Page/Page column 3; 6

98446-49-2 Synthesis

98446-49-2
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$6.00/1g

372-09-8
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$20.00/25g

538-75-0 Synthesis