34040-62-5Relevant academic research and scientific papers
One-pot method to construct isoindolinones and its application to the synthesis of DWP205109 and intermediate of Lenalidomide
Liu, Jinbiao,Lu, Bowei,Lu, Junrui,Wang, Hongbo,Xie, Zhiqiang,Zhong, Kaikai
supporting information, (2021/06/07)
Herein a practical and efficient system for concise synthesis of isoindolinones is described by using substituted methyl 2-(halomethyl)benzoates and substituted amines. Structurally various methyl 2-(halomethyl)benzoates and amines were transformed into isoindolinones 80–99% yield and purity in catalyst-free and solvent-free conditions. The method has a wide substrate scope. The synthetic utility of the one-pot reaction was demonstrated by the concise syntheses of Lenalidomide intermediate and DWP205190.
Production method of methyl o-formate benzyl sulfonamide
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Page/Page column 6-9, (2020/09/12)
The invention belongs to the technical field of pesticide intermediates, and particularly relates to a production method of methyl o-formate benzyl sulfonamide. The production method comprises steps:reacting o-methylbenzoic acid with sulfuryl chloride to obtain o-chloromethylbenzoic acid; reacting o-chloromethylbenzoic acid with methanol to obtain o-chloromethyl methyl benzoate; reacting o-chloromethyl methyl benzoate with sodium thiosulfate to obtain methyl o-formate benzyl mercaptan, reacting methyl o-formate benzyl mercaptan with chlorine to obtain methyl o-formate benzyl sulfonyl chloride, and reacting methyl o-formate benzyl sulfonyl chloride with ammonia gas to obtain methyl o-formate benzyl sulfonamide. According to the method, polychlorinated side reactions in the production process are reduced, the yield is increased, the tar yield is reduced, and the problems of low yield and high cost in the production process are solved.
Triggering a [2]rotaxane molecular shuttle through hydrogen sulfide
Yang, Shun,Luan, Zhoulin,Gao, Chuan,Yu, Jingjing,Qu, Dahui
, p. 306 - 310 (2017/09/06)
A novel chemically-controlled [2]rotaxane molecular shuttle was successfully designed and synthesized. A H2S-responsive bulk barrier was introduced between the two identical recognition stations of the [2]rotaxane to prevent dynamic shuttling of the macrocycle. Upon addition of H2S, the complete intramolecular cascade reaction occurs in a controllable manner, resulting in removal of the bulk barrier and the shuttling motion of the macrocycle between the two stations recovers.
Mild Aliphatic and Benzylic Hydrocarbon C-H Bond Chlorination Using Trichloroisocyanuric Acid
Combe, Sascha H.,Hosseini, Abolfazl,Parra, Alejandro,Schreiner, Peter R.
, p. 2407 - 2413 (2017/03/11)
We present the controlled monochlorination of aliphatic and benzylic hydrocarbons with only 1 equiv of substrate at 25-30 °C using N-hydroxyphthalimide (NHPI) as radical initiator and commercially available trichloroisocyanuric acid (TCCA) as the chlorine source. Catalytic amounts of CBr4 reduced the reaction times considerably due to the formation of chain-carrying ·CBr3 radicals. Benzylic C-H chlorination affords moderate to good yields for arenes carrying electron-withdrawing (50-85%) or weakly electron-donating groups (31-73%); cyclic aliphatic substrates provide low yields (24-38%). The products could be synthesized on a gram scale followed by simple purification via distillation. We report the first direct side-chain chlorination of 3-methylbenzoate affording methyl 3-(chloromethyl)benzoate, which is an important building block for the synthesis of vasodilator taprostene.
2-(4-METHOXYCARBONYLMETHYLPHENOXYMETHYL)BENZOIC ACID METHYL ESTER AND METHOD FOR PRODUCING THE SAME
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Page/Page column 7-8, (2009/06/27)
Dibenzoxepinacetic acid useful as an intermediate for pharmaceutical products can advantageously be produced by way of a method for producing methyl 2-(4-methoxycarbonylmethylphenoxymethyl)benzoate comprising a reaction of methyl 2-chloromethylbenzoate with methyl 4-hydroxyphenylacetate.
TERTIARY ALKYL ESTER OF OXODIBENZOXEPIN ACETIC ACID
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Page/Page column 10, (2009/07/17)
A tertiary alkyl ester represented by Formula (2): wherein R1 and R2 each independently represent a C1-4 alkyl group, and a method for producing the same.
Novel preparation of (2-azidomethyl)benzoic acid and an application as a protective group
Matsuda, Hiroko,Hashimoto, Masaru,Okuno, Toshikatsu
, p. 3347 - 3355 (2007/10/03)
A novel preparation method of 2-(azidomethyl)benzoic acid, a precursor of (2-azidomethyl)benzoyl (AZMB) protective group, was developed which can provide pure sample in gram scale without chromatographic purifications. Reductive cleavage using triphenylphosphine was found to be effective in the case of sterically hindered ester that resists under basic hydrolysis.
Development of an immunoassay for the residues of the herbicide bensulfuron-methyl.
Lee, Jae Koo,Ahn, Ki Chang,Park, Oee Sook,Ko, Yong Kwan,Kim, Dae-Whang
, p. 1791 - 1803 (2007/10/03)
To develop a competitive indirect enzyme-linked immunosorbent assay based on polyclonal antibodies for the detection of the sulfonylurea herbicide bensulfuron-methyl, seven structurally related haptens were synthesized. Four of them mimicking the target analyte were conjugated to keyhole limpet hemocyanin by the N-hydroxysuccinimide activated ester method to use as immunogens, and all of them were conjugated to bovine serum albumin to use as plate-coating antigens. Polyclonal antibodies raised in rabbits and the coating antigens were screened and selected for the assay in simple homologous and heterologous ELISA formats. Three sensitive heterologous ELISAs were selected and optimized, showing the average IC(50) values of bensulfuron-methyl as low as 0.17, 0.09, and 0.09 ng/mL, the detection ranges of 0.04-0.60, 0.01-0.60, and 0.04-0.25 ng/mL, and the lowest detection limits of 0.03, 0.002, and 0.03 ng/mL, respectively. The cross-reactivities of other sulfonylurea herbicides and metabolites of bensulfuron-methyl to the antibodies were less than 15% in the two assays. Recoveries from the analyte-fortified water samples in assay I were in the range of 81-125% by simple dilution. The correlation between the ELISA and HPLC was 0.999 (n = 15) with a slope of 1.37 in the analysis of groundwater samples fortified with bensulfuron-methyl. The results obtained strongly indicate that the ELISA can be a highly sensitive and convenient tool for detecting bensulfuron-methyl residues in agricultural and environmental samples.
Process for preparing o-(carboalkoxy)phenylmethanesulfonyl chloride derivatives
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, (2016/03/01)
A process for preparing an o-(carboalkoxy)phenylmethanesulfonyl chloride derivative of formula (1), wherein: X is chosen from a hydrogen atom, halogen atoms, C1to C6alkyl groups, C1to C6haloalkyl groups, C1to C6alkoxy groups, C1to C6alkoxycarbonyl groups, a nitro group, and a phenyl group; R is chosen from C1to C6alkyl groups, C1to C6haloalkyl groups, and C3to C6cycloalkyl groups; and n is chosen from integers ranging from 1 to 4, is discussed.
Generation and Thermal Reactions of 2-Methyl-4-oxo-2-selenoniochroman-3-ide
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Tsutsumi, Kazuhiro
, p. 1397 - 1400 (2007/10/02)
The thermal reaction of 2-methyl-4-oxo-2-selenoniochroman-3-ide (4) in aprotic solvents afforded (E)-bisbenzoyl>ethylene (5) and trans-1,2,3-trisbenzoyl>cyclopropane (6) via a carbene intermediate.Ethanol reacted thermally with 4 to open the chroman ring, giving ethyl 2-benzoate (9a) and ethyl 2-(ethoxymethyl)benzoate (10a), whereas reaction with methanol yielded only methyl 2-benzoate (9b).Hydrolysis of ylide 4 eliminated dimethyl selenide, giving phthalide and 2-(hydroxymethyl)benzoic acid.
