ChemicalBook CAS DataBase List Methyl 4-acetamido-5-chloro-2-methoxybenzoate

Methyl 4-acetamido-5-chloro-2-methoxybenzoate synthesis

9synthesis methods

Product Name:Methyl 4-acetamido-5-chloro-2-methoxybenzoate
CAS Number:4093-31-6
Molecular formula:C11H12ClNO4
Molecular Weight:257.67

4093-29-2

4093-31-6

General procedure for the synthesis of methyl 4-acetamido-5-chloro-2-methoxybenzoate from methyl 4-acetamido-2-methoxybenzoate: 136g of N,N-dimethylformamide (DMF) was added as solvent in a 1L reaction flask, followed by the addition of 50g of methyl 4-acetamido-2-methoxybenzoate, and stirred until it was completely dissolved. To the solution was added 50 g of N-chlorosuccinimide (NCS), which was slowly heated to 40 °C and the reaction was maintained at this temperature for 5 hours. The reaction temperature was then raised to 65 °C and the reaction continued for 4 hours. Upon completion of the reaction, the reaction mixture was cooled to 0 °C and thermo-crystallization was carried out for 8 h. The crude product of methyl 4-acetamido-5-chloro-2-methoxybenzoate was obtained, while the mother liquor of N,N-dimethylformamide was recovered. The crude product was dissolved in 100 g of deionized water, heated to 50 °C and kept for 4 hours, then cooled to 5 °C for filtration. The filtered solid was dried to obtain a white crystalline product, methyl 4-acetamido-5-chloro-2-methoxybenzoate 52.1 g, with a molar yield of 90.3% and HPLC purity ≥99.8%.

4093-29-2 Synthesis

4093-29-2
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$5.00/250mg

4093-31-6
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$8.00/5g

Yield:4093-31-6 90.3%

Reaction Conditions:

with N-chloro-succinimide in N,N-dimethyl-formamide at 40 - 65; for 9 h;Temperature;

Steps:

10 Example 10 (mother liquor sixth application)
The 136gN, N-dimethyl formamide stock solution to 1L in the reaction bottle, inputs 50g4-acetamido-2-methoxybenzoic acid methyl ester, the agitation dissolves clear, inputs 50gN-chloro succinimide, slow heating to 40 °C, thermal insulation reaction 5h, and then raising the temperature to 65 °C, thermal insulation reaction 4h; after the reaction, cooling to 0 °C thermal crystallization 8h, by the splash zone 4-acetamido-5-chloro-2-methoxybenzoic acid methyl ester crude wet product, N, reservations N-dimethyl formamide mother liquor; the 4-acetamido-5-chloro-2-methoxybenzoic acid methyl ester product added to the wet product 100g deionized water, the temperature is increased to 50 °C insulating 4h, cooling to 5 °C filtered, dried to obtain the kind of white 4-acetamido-5-chloro-2-methoxybenzoic acid methyl ester 52.1g, molar yield 90.3%, HPLC purity ≥ 99.8%.

References:

Jinan-double of the Chemical Co., Ltd;Wang, Wenxin;Li, Yuedong;Cao, Xiaohua;Liu, Xuewen;Wang, Yongguang CN105523952, 2016, A Location in patent:Paragraph 0029

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20896-27-9 Synthesis