41295-64-1

Usage

Uses

Used in Pharmaceutical Industry:
4-chloro-3-oxobutyryl chloride is used as a synthetic intermediate for the development of Amlodipine Besylate (A633500), a dihydropyridine calcium channel blocker. It serves as an antianginal and antihypertensive agent, helping to manage angina and high blood pressure by relaxing blood vessel walls and improving blood flow.
Used in Chemical Synthesis:
In the chemical industry, 4-chloro-3-oxobutyryl chloride is utilized in the preparation of Dioxohexanoate. This process involves the chlorination of Methyleneoxetanone, followed by condensation with Meldrum's acid and subsequent esterification. The resulting Dioxohexanoate can be further used in the synthesis of various chemicals and compounds.
Overall, 4-chloro-3-oxobutyryl chloride plays a significant role in both the pharmaceutical and chemical industries, contributing to the development of essential drugs and chemicals for various applications.

InChI:InChI=1/C4H4Cl2O2/c5-2-3(7)1-4(6)8/h1-2H2

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 56-23-5 tetrachloromethane 
• 7782-50-5 chlorine 
• 15159-48-5 2,4-oxetanedione 

Downstream Products

• 18592-13-7 6-chloromethyluracil 
• 39082-00-3 α-chloroacetoacetanilide 
• 147770-43-2 3-chloropyruvaldehyde-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]hydrazone 
• 4116-10-3 α-chloro-N-methylacetoacetamide 
• 27807-84-7 4-chloro-3-oxobutanoic acid 
• 1228365-47-6 C₁₀H₈ClF₂NO₂ 
• 912264-33-6 4-chloro-N-(2-fluoro-5-nitrophenyl)-3-oxobutyramide 
• 871267-25-3 C₁₁H₁₂ClNO₃ 
• 61610-54-6 4-chloro-3-oxo-N-(p-tolyl)butyramide 
• 400024-02-4 C₁₀H₉Cl₂NO₂ 
• 71919-02-3 4-Chloro-N-(4-methoxy-phenyl)-3-oxo-butyramide 
• 871267-32-2 C₁₀H₈Cl₃NO₂ 
• 1228365-48-7 C₁₂H₁₄ClNO₃ 
• 61610-51-3 4-chloro-3-oxo-N-(4-fluorophenyl)butaneamide 

Relevant academic research and scientific papers

Preparation method of ethyl 4-chloroacetoacetate

The invention discloses a preparation method of ethyl 4-chloroacetoacetate, which specifically comprises the following steps of: (1) chlorination: cooling dichloromethane for the first time, then adding acetyl ketene for cooling for the second time, then introducing chlorine gas, and keeping the temperature; (2) esterification: dropwise adding absolute ethyl alcohol, and keeping the temperature; (3) desolvation and deacidification: heating and distilling to remove dichloromethane and hydrogen chloride; and (4) rectification: rectifying and purifying to obtain the product. Acetyl ketene is used as a raw material, the raw material is low in cost and easy to obtain, the synthesis steps are simple, and the production cost is reduced; by optimizing the ratio of process materials, the selectivity of the product ethyl 4-chloroacetoacetate is improved, and the yield is increased; and through high-vacuum low-temperature distillation, the decomposition of the heat-sensitive product ethyl 4-chloroacetoacetate is effectively prevented, and the yield and the product quality are improved.

Preparation method of methyl 4-chloroacetoacetate

The invention discloses a preparation method of methyl 4-chloroacetoacetate, which specifically comprises the following steps: (1) chlorination: cooling dichloromethane for the first time, then adding ketene dimer for cooling for the second time, then introducing chlorine gas, and keeping the temperature; (2) esterification: dropwise adding absolute methanol, and keeping the temperature; (3) desolvation and deacidification: heating and distilling to remove dichloromethane and hydrogen chloride; and (4) rectification: rectifying and purifying to obtain the product. The diketene is used as the raw material, the raw material is low in cost and easy to obtain, the synthesis steps are simple, and the production cost is reduced; by optimizing the ratio of process materials, the selectivity of the product ethyl 4-chloroacetoacetate is improved, and the yield is increased; through high-vacuum low-temperature distillation, the decomposition of a heat-sensitive product ethyl 4-chloroacetoacetate is effectively prevented, and the yield and the product quality are improved.

Continuous device and method for industrial production 4 - chloroacetoacetate

The invention relates to an industrial production 4 - chloroacetoacetate continuous device and a method. The device and method can inhibit the generation of byproduct 2 - chloroacetoacetate and 4 - chloroacetoacetate in 2 - chloroacetoacetate crude product can be controlled below 0.15%. The yield of 4 - chloroacetoacetate can be improved, and the yield 4 - chloroacetoacetate can reach 97% or more. The continuous device and the method provided by the invention can be operated continuously, 4 - chloroacetoacetate can be industrially produced, and the continuous device has remarkable economic value.

A 4-chloro-acetyl-acetic acid ethyl ester preparation method

The invention relates to a preparation method of 4-chloracetyl ethyl acetate. The preparation method comprises the following steps: by taking diketene as an initial raw material, synthesizing a 4-chloracetyl ethyl acetate coarse product in two steps: chlorination and esterification; then, rectifying to obtain a finished product, and adding a stabilizer anhydrous cupric sulfate into the chlorination step, wherein the addition is 0.02-1wt% of diketene. Compared with the prior art, the preparation method provided by the invention has the advantages that 1, by adding the stabilizer anhydrous cupric sulfate, the production of a byproduct 2-chloracetyl ethyl acetate is reduced and the production of the byproduct 2-chloracetyl ethyl acetate in the 4-chloracetyl ethyl acetate coarse product can be controlled below 0.5%, so that the distill yield is greatly improved; 2, the yield of 2-chloracetyl ethyl acetate is over 94.5%, and the cost is greatly lowered.

PREPARATION OF 3,5-DIOXO HEXANOATE ESTER IN TWO STEPS

The invention discloses a method for the preparation of tert-butyl 6-chloro-3,5- dioxohexanoate from Meldrum's acid derivative and its use for the preparation of tert-butyl (4R,6S)-(6-hydroxymethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetate(BHA), Rosuvastatin and Atorvastatin.

Process for the production of 4-chloroacetyl chloride, 4-chloroacetic acid esters, amides and imides

The invention relates to process for the continuous production of 4-chloroacetoacetyl chloride, comprising the steps of (a) feeding diketene and chlorine into a thin film reactor and (b) reacting the diketene and chlorine to obtain 4-chloroacetoacetyl chloride. The invention also relates to a process for the production of 4-chloroacetic acid ester, 4-chloroacetic acid amide or 4-chloroacetic acid imide from 4-chloroacetoacetyl chloride obtained according to the inventive process.

Study of thiazoline derivatives for the design of optimal fungicidal compounds using multiple linear regression (MLR)

Rice blast is the most serious disease of rice due to its harmfulness and its world wide distribution. Magnaporthe grisea is the cause of rice blast disease and destroys rice enough to feed several tens of millions of people each year. Fungicides are commonly used to control rice blast. But M. grisea acquires resistance to chemical treatments by genetic mutations. 2-Phenylimino-1,3-thiazolines were proposed as a novel class of fungicides against M. grisea in the previous study. To develop compounds with a higher biological activity, a new series of 2-phenylimino-1,3-thiazolines was synthesized and its fungicidal activity was determined against M. grisea. The QSAR analysis was carried out on a series of 2-phenylimino-1,3-thiazolines. The QSAR results showed the dependence of fungicidal activity on the structural and physicochemical features of 2-phenylimino- 1,3-thiazolines. Our results could be used as guidelines for the study of the mode of action and further design of optimal fungicides. Copyright

Exploration of novel 2-alkylimino-1,3-thiazolines: T-type calcium channel inhibitory activity

We have developed combinatorial libraries of new 2-alkylimino-1,3- thiazolines with four diversity points, consisting of more than 500 compounds, in a parallel synthetic fashion. The synthetic strategy was based on the construction of a large library aimed at the discovery of new compounds with T-type calcium channel inhibitory activity through structure modifications of hit compound 2. The syntheses of the compounds of Chemset A with four diversity points were accomplished by the condensation of thioureas 5 with α-haloketones 6{1-66} having two diversity points each. A library of phthalimidyl 1,3-thiazolines 24 was synthesized to provide Chemset B, which allowed the introduction of other diversity points through the nucleophilic character of the amino nitrogen. A sublibrary, Chemset C, was constructed from the libraries of Chemset A and Chemset B by functionalization of the C-4 position of the 1,3-thiazoline ring. The products containing ester or acid groups at the C-4 position of the 1,3-thiazoline ring were used in amide synthesis to give a new sublibrary within Chemset C. Deprotection of the phthalimidyl moiety of 24 followed by the reaction with benzoyl chloride gave the corresponding sublibrary in Chemset C. Another sublibrary which includes secondary amino derivatives was obtained by reduction of the amide moiety or reductive amination of 23 with phenyl aldehyde. The selected compounds from the generated libraries were evaluated with respect to inhibition of T-type calcium channels, where some of them have exhibited promising activity.

NOVEL CRYSTAL OF 7- 2-(2-AMINOTHIAZOLE-4-YL)-2-HYDROXYIMINOA CETAMIDO-3-VINYL-3-CEPHEM-4-CARBOXYLIC ACID (SYN ISOMER) AND METHOD FOR PREPARATION THEREOF

A novel crystal (B-type crystal) of 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide-3-vinyl-3-cephem-4-carboxylic acid (a syn isomer), characterized in that it exhibits peaks at diffraction angles shown in the following Table 1, in its powder X ray diffraction pattern: This crystal is obtained by forming a crystal from a solution at a temperature of -5 to 5°C in an acidic state. The crystal is not bulky, exhibits good stability and good filterability, and is excellent in the solubility toward water, and thus can be prepared with case.

Crystalline 7-(2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4-carboxylic acid (syn isomer)

The invention relates to crystalline 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) useful as an antimicrobial agent.