[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Names and Identifiers

Name	2,4-Dihydro-4-[[4-(4-Hydroxyphenyl)-1-Piperazinyl]-Phenyl]-2-(1-Methylpropyl)-3H-1,2,4-Triazole-3-On
Synonyms	CIS-DTM Cis -Mesylate Cis-trimesylate [2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate Cis-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Ylmethyl Methanesulphonate 2,4-Dihydro-4-[[4-(4-Hydroxyphenyl)-1-Piperazinyl]-Phenyl]-2-(1-Methylpropyl)-3H-1,2,4-Triazole-3-On CIS-[2-(2,4-DICHLOROPHENYL)-2-(1,2,4-TRIAZOL-1-YL-METHYL)-1,3-DIOXOLAN-4-YL]METHYL METHANESULPHONATE CIS-[2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL] METHYL METHANESULFATE 2,4-dihydro-4-[[4-(4-hydroxyphenyl)-1-piperazinyl]-phenyl]-2-(1-methylpropyl)-3h-1,2,4-triazole-3-one CIS-[2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL]METHYL METHANESULFONATE 1-[[(2r,4s)-2-(2,4-dichlorophenyl)-4-(methylsulfonyloxymethyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole [(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate [(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate 1,3-DIOXOLANE-4-METHANOL, 2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-METHANESULFONATE(ESTER),(2R,4R)-REL-
CAS	67914-86-7
EINECS	267-749-5
InChI	InChI=1/C14H15Cl2N3O5S/c1-25(20,21)23-6-11-5-22-14(24-11,7-19-9-17-8-18-19)12-3-2-10(15)4-13(12)16/h2-4,8-9,11H,5-7H2,1H3

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Physico-chemical Properties

Molecular Formula	C14H15Cl2N3O5S
Molar Mass	408.25
Density	1.59±0.1 g/cm3(Predicted)
Melting Point	98 °C
Boling Point	615.5±65.0 °C(Predicted)
Flash Point	326°C
Solubility	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Vapor Presure	4.42E-15mmHg at 25°C
Appearance	Solid
Color	White to Off-White
pKa	2.94±0.12(Predicted)
Storage Condition	2-8°C
Refractive Index	1.647

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Reference Information

preparation

a CIS 2(2,4 dichlorophenyl) 2([1,2, the synthesis method of 4] triazole 1 methyl)[1,3] dioxolane 4 Methyl methanesulfonate comprises the following steps:(1) Firstly, M-dichlorobenzene is used as a raw material, and bromoacetyl bromide is reacted with each other;(2) Condensation with glycerol catalyzed by heteropolyacid TiSiW12O40/SiO2;(3) esterification with benzoyl chloride;(4) Condensation with 1,2,4 triazole catalyzed by sodium carbonate, the CIS alcohol is obtained after hydrolysis and recrystallization;(5) the product is obtained by esterification with methanesulfonyl chloride. The reaction equation was as follows: 1) synthesis of 2 Bromo 1(2,4 dichlorophenyl) ethanone into a 1.12 ml three-necked flask were placed 150g(1.00mol) of anhydrous aluminum trichloride, and 147G (mol) of M-dichlorobenzene were added, after stirring at room temperature, Bromo-Acetyl bromide 201g(1.00mol) was slowly added dropwise, the mixture was further stirred at room temperature for 30 minutes, slowly raised to 5055 ° C., and stirred at this temperature for 5 hours, the reaction solution was poured into ice water to ice, cooled to room temperature, extracted twice with 500ml dichloromethane, combined with dichloromethane extract, washed with water until neutral, dried over anhydrous sodium sulfate, filtered to recover solvent, the residue was reconstituted to give 240g of a white irritating solid in a yield of 90.0%. 2) synthesis of intermediate I to a 1000mL four-necked flask, 268g of the solid obtained in the previous step, 92g of glycerol, toluene and catalyst TiSiW12O40/SiO21.3g were added, and the mixture was heated to reflux for azeotropic dehydration, (Subject to failure to separate water). After completion of the reaction, the catalyst was recovered by filtration and recycled after regeneration. The mother liquor was washed with potassium hydroxide, dried over anhydrous MgSO4, and the solvent was recovered under reduced pressure to obtain a yellow oily substance (which can be analyzed by GC) with a yield of 94%. 3) synthesis of cis-Bromo Ester triethylamine was added to a 1000ml Four-necked flask, and then the above bromide was pumped into 341G, stirred and dissolved, and then cooled to below 10 ° C., benzoyl chloride was added dropwise, and dropped for about 3 hours. After dropping, the reaction was continued at 30 ° C. For 2 hours, and triethylamine was recovered under reduced pressure. Then water and chloroform were added, layers were separated, and the organic phase was washed with hydrochloric acid and dried over anhydrous Na2SO4, After chloroform was recovered under reduced pressure, an oil was obtained, methanol was added, and after stirring, a solid was precipitated, Suction filtration and drying were performed to obtain a crude product, and then methanol was recrystallized to obtain 260g of cis-Bromo Ester, yield 58%,mp:117120 °c. 4) synthesis of cis-alcohol DMF, cis-Bromo Ester 446G, 1,2,4 triazole 69G, sodium carbonate 53g were added to a 1000ml Four-necked flask, stirred and heated to reflux, then water was added, 30% Lye, after 2 hours of heat preservation, cooled to 30 degrees Celsius, stirred for 1 hours, centrifuged, washed with water and dried to obtain crude CIS alcohol. The crude product was recrystallized from toluene and methanol, filtered and dried to obtain G of cis-alcohol product, yield 62%,mp:135140 ℃. 5) synthesis of methanesulfonic acid active ester triethylamine was added to a 1000ml Four-necked flask, then cis-alcohol was added, stirred, dissolved and cooled to 5 ℃, then methanesulfonyl chloride was added dropwise, and the temperature was raised to 25 ℃ after addition, the solvent was recovered after 5 hours of incubation, After stirring for 5 hours with proper amount of water, filtering, washing, drying and recrystallization to give 359g of CIS 2(2,4 dichlorophenyl) 2([1,2,4] triazole 1 methyl). [1,3] dioxolane 4 Methyl methanesulfonate as a white or off-white solid in 88% yield.

Application

CIS 2(2,4 dichlorophenyl) 2([1,2,4] triazole 1 methyl)[1,3] dioxolane 4 methyl mesylate is an important intermediate for the synthesis of antifungal drugs, and is also an essential intermediate for the synthesis of itraconazole, which is of great significance to the research and development of its new synthesis process.

Last Update：2024-04-09 21:11:58

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate

Changsha Changtang import and Export Co., Ltd.

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate

2,4-Dihydro-4-[[4-(4-Hydroxyphenyl)-1-Piperazinyl]-Phenyl]-2-(1-Methylpropyl)-3H-1,2,4-Triazole-3-On

CAS: 67914-86-7

Molecular Formula: C14H15Cl2N3O5S

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Names and Identifiers

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Physico-chemical Properties

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Reference Information

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[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate Request for Quotation

2,4-Dihydro-4-[[4-(4-Hydroxyphenyl)-1-Piperazinyl]-Phenyl]-2-(1-Methylpropyl)-3H-1,2,4-Triazole-3-On

CAS: 67914-86-7

Molecular Formula: C14H15Cl2N3O5S

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Names and Identifiers

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Physico-chemical Properties

[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate - Reference Information

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[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate