ChemicalBook CAS DataBase List Chlorambucil

Chlorambucil synthesis

6synthesis methods

Product Name:Chlorambucil
CAS Number:305-03-3
Molecular formula:C14H19Cl2NO2
Molecular Weight:304.21

Chlorambucil, 4-[p-[bis-(2-chloroethyl)amino]phenyl]butyric acid (30.2.1.7), is made from acetanilide and succinic anhydride. In the first stage of synthesis, acetanilide is acylated by succinic anhydride, giving 4-(4-acetaminophenyl)-4-ketobutyric acid (30.2.1.3). The keto group in this compound is reduced by hydrogen in a methanol solution using palladium on carbon as a catalyst. This results in the formation of the methyl ester of 4-(4-acetaminophenyl)-butyric acid (30.2.1.4). This is treated with an alkali in order to hydrolyze both the amide and ester parts of the molecule, which forms 4-(4-aminophenyl)butyric acid (30.2.1.5), which upon reaction with ethylene oxide gives 4-[p-[bis(2-hydroxyethyl) amino]phenyl]butyric acid (30.2.1.7). Replacing all of the hydroxyl groups in this compound using phosphoryl chloride and subsequent treatment with water to hydrolyze the resulting intermediate acid chloride to an acid gives chlorambucil (30.2.1.7).

2033-24-1 Synthesis

2033-24-1
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Benzeneacetaldehyde, 4-[bis(2-chloroethyl)amino]-

500590-36-3
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305-03-3
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Yield:305-03-3 76.9%

Reaction Conditions:

with formic acid;triethylamine at 50 - 95; for 5 h;Temperature;

Steps:

2.4 Example 2

(4) 304 g of triethylamine was slowly added dropwise to 680 g of the 920 formic acid system.After 5 h, the reaction was stirred at 50 °C for 2 h. To the system, 156 g of 4-[bis(2-chloroethyl)amino]phenylacetaldehyde was added in 7 batches.Lastly, we added 87g of Mie acid,The temperature was raised to 95 °C and the reaction was completed for 5 h. Transfer the system to water,Extract twice with 500 g of dichloromethane, wash once with 1000 g of water, and wash once with 500 g of saturated brine.The organic phase was separated, dried, and the solvent was evaporated in vacuo to give 172 g of a crude oil.Recrystallization from a mixed solvent of 500 g of dichloromethane and 200 g of petroleum ether gave 139 g of chlorambucil.White crystals.Yield 76.9%,The content is 99.2%.

References:

CN107628962,2018,A Location in patent:Paragraph 0027; 0039; 0040; 0045

79481-83-7 Synthesis