83857-96-9Relevant articles and documents
Iodine as a chemoselective reoxidant of TEMPO: application to the oxidation of alcohols to aldehydes and ketones.
Miller, Ross A,Hoerrner, R Scott
, p. 285 - 287 (2003)
[reaction: see text] Chemoselective alcohol oxidations using catalytic TEMPO and stoichiometric iodine as the terminal oxidant were studied. Iodine was compared to other positive halogens as the terminal oxidant and shown to be superior in cases of electron-rich and heteroaromatic rings. The new conditions were successfully applied to an important intermediate (2) in the synthesis of Losartan.
Preparation method of 2-n-butyl-4-chloro-5-formyl imidazole
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Paragraph 0066-0068, (2020/09/09)
The invention discloses a preparation method of 2-n-butyl-4-chloro-5-formyl imidazole, and relates to a preparation method of 2-n-butyl-4-chloro-5-formyl imidazole. The method comprises the followingsteps: (1) cyclizing valeraldehyde and pyruvic aldehyde to obtain 2-butyl-5-methylimidazole; (2) carrying out chlorination reaction on the 2-butyl-5-methylimidazole to prepare 2-butyl-4-chloro-5-methylimidazole; and (3) carrying out an oxidation reaction on the 2-butyl-4-chloro-5-methylimidazole to obtain 2-n-butyl-4-chloro-5-formyl imidazole of which the structure is as shown in a formula I whichis described in the specification.
Production process of imidazole aldehyde
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Paragraph 0048-0074, (2019/07/11)
The invention provides a production process of imidazole aldehyde. Imiline is prepared by using valeronitrile and methanol as raw materials, glycine and methanol are added to prepare imidic acid, anda further reaction is conducted with phosphorus oxychloride and DMF to obtain the imidazole aldehyde. By controlling reaction conditions and the feed ratio of the raw materials, the formation of by-products is reduced, and the yield is improved. A decoking and decolorization reaction and an activated carbon decolorization reaction are adopted, the solubility change of the imidazole aldehyde underdifferent pH conditions is used for purifying a product, and finally, the imidazole aldehyde with a purity of more than 99.2% is obtained by recrystallization.
Method for recovering and utilizing byproduct of chlorination of phosphorus pentachloride
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Paragraph 0038-0039, (2017/08/28)
The invention relates to a technology for comprehensively utilizing the byproduct of chlorination of phosphorus pentachloride, and mainly relates to a post treatment, which scientifically utilizes the excess phosphorus pentachloride reagent. The byproduct is converted into an organic synthesis reagent with a wide application range. The wastes are converted into a valuable resource. The discharge of waste water, waste gas, and waste solid is reduced. The obtained reagent is an excellent active reagent, which is widely used in the chemical industry, pharmacy industry, and material industry. The production cost is reduced, and the environment is protected.
Preparation method of 2-n-butyl-4-chloro-5-formylimidazole
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Paragraph 0042-0050, (2017/08/31)
The invention provides a preparation method of 2-n-butyl-4-chloro-5-formylimidazole. The preparation method comprises the following steps of using pentanimidamide hydrochloride and tert-butyl glycine hydrochloride as initial raw materials to react, so as to obtain (1-imido amyl)tert-butyl glycinate; performing deprotection, ring closing, chlorinating and vilsemier reaction, and recrystallizing, so as to obtain the 2-n-butyl-4-chloro-5-formylimidazole. The preparation method has the advantages that the price of raw materials is low, the obtaining is easy, the cost is low, the content of impurities is low, and the purity is high; the organic solvent used in the preparation process can be recycled, the pollution is little, the environment-friendly effect is realized, and the preparation method is suitable for industrialized large-scale production.
An efficient and green synthetic route to losartan
Shuangxia, Feng,Zheng, Gu,Yelv, Tang,Hui, Liu,Guofang, Jiang
, p. 451 - 454 (2015/11/03)
A practical, efficient and green process for the preparation of losartan, an antihypertensive drug, has been developed with an overall yield of 58.6%. The key step is the synthesis of the two key intermediates 2-butyl-4-chloro-3H-imidazole-5-carbaldehyde (BCFI) and 2-cyano-4'-methyl biphenyl (OTBN). BCFI was synthesised from valeronitrile and acetyl chloride by three steps with an overall yield of 69%; OTBN was obtained in 86% yield by the coupling of o-chlorobenzonitrile with p-methylphenylmagnesium chloride in tetrahydrofuran in the presence of manganese chloride and chlorotrimethylsilane. The above route was successfully operated in at a pilot-plant operation.
Preparation of 2-Substituted 4-Chloro-5-Formylimidazole and 5-Formylimidazole
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Page/Page column 4-5, (2008/12/08)
The invention relates to a preparation process for 2-substituted 5-formylimidazoles, wherein the intermediate high-pressurized synthesis of an 2-substituted 4-hydroxymethylimidazole as known in the art is conveniently avoided, and wherein much higher yields are obtained. Instead, it is proposed to prepare such 2-substituted 5-formylimidazoles via a one-pot synthesis involving 2-substituted 4-chloro-5-formylimidazole, thereby employing an additional hydrodehalogenation step. Moreover, it is found that the yield and purity of 2-substituted 4-chloro-5-formylimidazole itself can be significantly improved using a triflate catalyst in the preparation process.
Process for preparing 2,4,5-trisubstituted imidazoles from N-acylated alpha-amino nitriles
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Page 5, (2008/06/13)
The invention is a process for preparing an imidazole of formula I which comprises treating an N-acylated α-amino nitrile with a phosphine and a carbon tetrahalide of the formula CX4, wherein X is Cl or Br, to form a haloimidazole of the formula wherein R1 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2-aryl, and aryl; and R2 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2—O-aryl and aryl; and X is selected from the group consisting of Cl and Br.
A rapid and efficient synthesis of 2-butyl-5-chloro-3H-imidazole-4- carboxaldehyde
Srinivas,Snehalatha Nair,Ramesh,Pardhasaradhi
, p. 506 - 508 (2007/10/03)
A rapid, efficient, cost effective procedure has been developed for the synthesis of 2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde. Preparation of methyl pentanimidate was accomplished in just 12 hours, followed by a sequence of reactions without isolation and purification of the formed intermediates. The final compound was purified by simple acid-base treatment to get a product with 99.9% HPLC purity.
Crystal structures of two imidazole derivatives
Ambalavanan,Palani,Ponnuswamy,Thirumuruhan,Yathirajan,Prabhuswamy,Raju,Nagaraja,Mohana
, p. 75 - 82 (2007/10/03)
2-n-Butyl-5-chloro-3H-imidazole-4-carbaldehyde (BCIC), C8H 11ClN2O. F.W.= 186.64, monoclinic, P21/c, a=7.2617(3)A, b= 13.2067(6)A, c=9.8491(4)A β = 101.76(1)°, V= 924.74(7)A3, Z=4, Dcal = 1.341 Mgm-3, μ = 0.367mm-1, F000=392, λ (MoKα) = 0.71073A, final R1 and wR2 are 0.049 and 0.126, respectively. 2-n-Butyl-4-chloro-1 [(2-cyanobiphenyl-4-yl)methyl]-5- hydroxymethyl imidazok (BCCI), CvfliufilNnO, F.W. = 379.88, triclinic, P 1 a = 8.198(2)A, b = 10.997(3)A, c = 11.524(2)A, α= 90.83(2)°, β= 94.31(2)°, γ = 109.45(2)°, V= 976.0(2)A3, Z=2, Dcal = 1.293Mgm-3, μ = 1.856mm-1, F000 = 400, λ (CuKα) = 1.5418A, final R1 and wR2 are 0.081 and 0.239, respectively. The imidazole ring in both the molecules is planar. The n-butyl group adopts a bent conformation in BCIC where it is in extended conformation in BCCI. The biphenyl ring system orients at an angle of 45.1(1)° in BCCI. The molecules are stabilized by N-H...N and O-H... N type hydrogen bonds in addition to van der Waals forces.
