Burgess Reagent Synthesis CAS 29684-56-8

Shaanxi BLOOM Tech Co., Ltd. yog ib tug ntawm cov uas paub txog manufacturers thiab lwm tus neeg ntawm burgess reagent synthesis cas 29684-56-8 nyob Suav teb. Txais tos rau cov lag luam wholesale bulk zoo burgess reagent synthesis cas 29684-56-8 muag ntawm no los ntawm peb lub hoobkas. Kev pabcuam zoo thiab tus nqi tsim nyog muaj.

Burgess Reagent SynthesisFeem ntau yog ua tiav hauv cov kauj ruam no: Ua ntej, chlorosulfonyl isocyanate (ClSO₂NCO) yog reacted nrog anhydrous methanol ntawm qhov kub thiab txias (-78℃rau 0 degree) hauv anhydrous diethyl ether los yog dichloromethane los tsim methyl chlorosulfonyl carbamate (ClSO₂NHC). Cov kauj ruam no yuav tsum muaj kev tswj xyuas nruj ntawm cov dej noo; Tom ntej no, triethylamine yog ntxiv dropwise rau cov tshuaj tiv thaiv kab mob nyob rau hauv ib tug inert cua, reacting nrog rau nruab nrab los ua ib tug crystalline khoom. Qhov kub yuav tsum tau khaws cia qis dua 0℃kom tsis txhob muaj kev cuam tshuam sab nraud; Tom qab cov tshuaj tiv thaiv tiav lawm, cov ntsev triethylamine hydrochloride raug tshem tawm los ntawm kev pom, thiab cov filtrate yog concentrated nyob rau hauv lub siab txo kom tau ib tug dawb mus tawm - dawb khoom crude khoom. Thaum kawg, high-purity Burgess reagent yog tau los ntawm recrystallization (feem ntau yog siv ib tug sib tov ntawm anhydrous ether thiab pentane li cov kuab tshuaj) los yog kem chromatography purification. Tag nrho cov txheej txheem synthesis yuav tsum nruj me ntsis tiv thaiv los ntawm noo noo, vim tias cov reagent no tsis tshua muaj siab rau dej. Cov txiaj ntsig feem ntau yog nyob nruab nrab ntawm 60-80%. Nws cov qauv tuaj yeem ua tus cwj pwm los ntawm ¹H NMR (δ 1.2-1.4 ppm rau ntau lub ncov ntawm triethylmethyl, δ 3.7 ppm rau ib lub ncov ntawm methoxy) thiab IR (muaj zog carbonyl absorption ncov ze 1720 cm⁻¹). Qhov no reagent yog dav siv los ua ib tug muaj zog lub cev qhuav dej nyob rau hauv cov organic transformation tshuaj xws li lub cev qhuav dej ntawm cawv rau alkenes thiab lub cev qhuav dej ntawm amides rau nitriles.

Melting point 76-79℃C (lit.), Qhov ntom 1.3023 (kev kwv yees ntxhib), Refractive index 1.6300 (kwv yees), Cia tej yam kev mob - 20℃C, Solubility nyob rau hauv organic solvents, Morphology siv lead ua hmoov, Xim me ntsis daj, rhiab heev, BRN 1432131, InChIKeyYSHOWEKUVWPFNR-UHFFFAOYSA-N, Hazard symbol (GHS), GHS07, Warning word, Hazard description h315-h319-h335, Precautions p264-p280-p302 + p{7} p{15} p362 + p364-p305 + P351 + P338 + P337 + p313-p261-p305 + P351 + p338-p280a-p304 + p340-p305-p501a, Kos npe zoo, / 38, Cov lus qhia kev nyab xeeb 26-36-37 / 39, WGK Lub Tebchaws Yelemees 3, F 10-21, TSCA No

Synthesis Method ntawm Burgess Reagent

Burgess Reagent (lub npe tshuaj: N-(Triethylammonium Sulfon 酰) Aminomethanoic Acid Methyl Ester, los yog Methyl Ester ntawm Methoxycarbonyl Sulfonamide Triethylammonium Inner Salt) yog ib qho me me thiab muaj txiaj ntsig zoo nruab nrab lub cev qhuav dej. Nws cov txheej txheem synthesis yuav tsum nruj me ntsis ua raws li qhov tsis muaj dej kom tsis txhob decomposition ntawm cov reagent. Cov hauv qab no yog cov kauj ruam tseem ceeb synthesis thiab cov ntsiab lus tseem ceeb:

Raw khoom npaj

Cov ntaub ntawv tseem ceeb suav nrog chlorosulfonated isocyanate (ClSO₂NCO), methanol (MeOH), thiab triethylamine (Et₃N). Tag nrho cov kuab tshuaj (xws li benzene thiab toluene) yuav tsum tau kho nrog cov tshuaj tsis muaj dej (xws li molecular sieve ziab lossis sodium hlau reflux), thiab cov hlab ntsha cov tshuaj tiv thaiv yuav tsum tau qhuav kom huv si thiab ntim nrog cov roj inert (xws li nitrogen) rau kev tiv thaiv.

 

Thawj cov tshuaj tiv thaiv: Esterification ntawm chlorosulfonated isocyanate thiab methanol

Ntawm qhov kub thiab txias (0-5 degree), maj mam ntxiv chlorosulfonated isocyanate rau anhydrous methanol dropwise los tsim cov intermediate methoxycarbonyl sulfonyl chloride (MeOCOSO₂Cl). Cov kauj ruam no yuav tsum muaj kev tswj hwm nruj ntawm qhov sib ntxiv kom tsis txhob muaj cua sov hauv zos thiab ua rau muaj kev cuam tshuam sab nraud. Tom qab cov tshuaj tiv thaiv ua tiav, tshem tawm cov tshuaj methanol uas tsis muaj kev cuam tshuam los ntawm lub tshuab nqus tsev distillation kom tau txais cov purified nruab nrab.

 

Qhov thib ob cov tshuaj tiv thaiv: Quaternization ntawm intermediate nrog triethylamine

Solub nruab nrab methoxycarbonyl sulfonyl chloride hauv anhydrous benzene thiab ntxiv triethylamine dropwise nyob rau hauv ib da dej dej khov. Cov tshuaj tiv thaiv tam sim no ua rau dawb precipitate (Burgess Reagent) thiab tso tawm hydrogen chloride (HCl). Sau cov precipitate los ntawm kev pom thiab ntxuav nws ntau zaus nrog cov benzene txias kom tshem tawm triethylamine uas tsis muaj kev cuam tshuam thiab los ntawm - khoom. Thaum kawg, qhuav cov khoom ntawm qhov kub qis hauv lub tshuab nqus tsev kom tau txais siab -purity Burgess Reagent (melting point 71-72℃).

 

Cia tej yam kev mob

Lub Burgess Reagent yog qhov tsis tshua muaj siab rau huab cua thiab noo noo thiab yuav tsum tau muab cia rau hauv qhov chaw tsis muaj roj nyob hauv qab -20℃txhawm rau tiv thaiv kev puas tsuaj thiab poob.

Kev siv tseem ceeb ntawm Burgess Reagent

 

Lub ntsiab daim ntawv thov ntawmBurgess Reagent Synthesisyog raws li ib tug dehydrating agent. Nws txhawb nqa lub cev qhuav dej ntawm cov pab pawg ua haujlwm xws li cawv thiab amides nyob rau hauv cov mob me me (los ntawm qhov kub thiab txias mus rau chav sov), thiab tshwj xeeb tshaj yog haum rau cov substrates uas nkag siab rau cov kua qaub lossis cov hauv paus. Cov hauv qab no yog nws cov xwm txheej ntawm daim ntawv thov thiab cov ntsiab lus ua haujlwm:

Cawv lub cev qhuav dej kom tsim alkenes

Lub Burgess Reagent tuaj yeem ua kom muaj txiaj ntsig zoo rau cis- lub cev qhuav dej ntawm cov cawv thib ob, ua kom muaj ob daim ntawv cog lus. Piv txwv li, thaum synthesizing macrolide compounds, kho -hydroxy carbonyl compounds nrog Burgess Reagent tuaj yeem xaiv tsim cis-alkenes, zam kev poob ntawm stereoselectivity los ntawm cov txheej txheem ib txwm muaj (xws li acid catalysis). Thaum lub sijhawm ua haujlwm, lub substrate yog yaj nyob rau hauv anhydrous dichloromethane (DCM), 1.0-1.5 sib npaug ntawm Burgess Reagent ntxiv, thiab cov tshuaj tiv thaiv yog nplawm ntawm chav tsev kub rau ob peb teev mus rau hmo ntuj. Tom qab cov tshuaj tiv thaiv tiav, cov khoom yog purified los ntawm silica gel kem.

Hydroxyl amide cyclization thiab lub cev qhuav dej los tsim oxazoles

Rau hydroxyl amides (xws li derivatives ntawm serine los yog threonine), Burgess Reagent tuaj yeem txhawb kev sib xyaw ua ke ntawm intramolecular, tsim 4,5-dihydroxazoles (2-oxazoline). Piv txwv li, thaum synthesizing intermediate tebchaw ntawm cov tshuaj tiv thaiv kab mob, kho hydroxyl amides nrog Burgess Reagent tuaj yeem tsim cov pob txha oxazole zoo. Cov tshuaj tiv thaiv zoo ib yam li cov dej cawv thib ob, tab sis lub sij hawm tshuaj tiv thaiv yuav tsum tau tswj kom tsis txhob tsim cov pyridine-type by-products vim lub cev qhuav dej ntau dhau.

Amine dehydration los tsim nitriles

Burgess Reagent kuj tseem siv tau rau lub cev qhuav dej ntawm thawj amines los tsim cov tshuaj nitrile. Piv txwv li, thaum synthesizing glutamine derivatives, kho cov amine nrog Burgess Reagent tuaj yeem xaiv tsim cov pab pawg nitrile thaum khaws lwm cov pab pawg rhiab heev (xws li ester pawg lossis halogens) hauv cov molecule. Cov tshuaj tiv thaiv no yuav tsum tau ua ntawm qhov kub qis (0-5 degree) txhawm rau txo cov kev mob tshwm sim.

Cov ntawv thov tsis yog- lub cev qhuav dej

Cov kev tshawb fawb tsis ntev los no tau pom tias Burgess Reagent kuj tuaj yeem siv tsis yog - cov tshuaj tiv thaiv lub cev qhuav dej, xws li kev sib xyaw ntawm sulfonyl amide esters los ntawm 1,2-diol lossis epoxy alcohols, kev sib xyaw ntawm - thiab -glycosylamines los ntawm carbohydrates, thiab cov synthesis ntawm cyclicoliquedes- sulfonamides. Cov tshuaj tiv thaiv no siv qhov tshwj xeeb reactivity ntawm Burgess Reagent, nthuav nws daim ntawv thov nyob rau hauv cov organic synthesis.

Burgess ReagentSynthesisyog ib qho me me thiab xaiv lub cev qhuav dej siv dav siv hauv cov khoom sib xyaw ua ke, tshwj xeeb tshaj yog tsim rau lub cev qhuav dej ntawm cov cawv los tsim cov alkenes. Nws cov txheej txheem tsim khoom yuav tsum tau ua raws li kev cai nruj rau cov dej tsis huv kom ntseeg tau tias kev ruaj ntseg thiab kev ua haujlwm ntawm cov reagent. Hauv qab no yog cov ncauj lus kom ntxaws txog kev tsim khoom ntawm Burgess Reagent:

Anhydrous mob

 

Burgess Reagent yog rhiab heev rau cov dej noo. Tag nrho cov khoom siv raw thiab cov kuab tshuaj yuav tsum tau qhuav kom huv si, thiab cov tshuaj tiv thaiv cov hlab ntsha yuav tsum tau qhuav thiab ntim nrog cov roj inert rau kev tiv thaiv.

Kev Tswj Kub Kub

 

Ob qho tshuaj tiv thaiv esterification thiab quaternary ammonium tsim cov tshuaj tiv thaiv yuav tsum tau nqa tawm ntawm qhov kub thiab txias kom tsis txhob muaj kev cuam tshuam sab thiab reagent decomposition.

Ntxiv Ceev

Hauv cov tshuaj tiv thaiv esterification thiab quaternary ammonium tsim cov tshuaj tiv thaiv, kev tswj hwm nruj ntawm qhov sib ntxiv yuav tsum tau ua kom ntseeg tau tias qhov sib xws thiab kev tswj hwm ntawm cov tshuaj tiv thaiv.

Cov khoom cia

 

Burgess Reagent yuav tsum tau muab ntim rau hauv ib qho chaw tsis muaj roj nyob ntawm qhov kub thiab txias (hauv qab -20 degree) kom tsis txhob decomposition thiab poob.

 

1. Lub Burgess reagent yog dab tsi?
Nws yog ib qho me me thiab ua tau zoo nrog lub cev qhuav dej, nrog cov tshuaj npe methyl chloroformylaminoformate methyl ester. Nws yog siv los xaiv lub cev qhuav dej, 1,2-diol thiab amides rau hauv alkenes, ethylene oxide thiab nitriles feem.
2. Dab tsi yog cov kauj ruam tseem ceeb ntawm nws?
Txoj kev siv hluavtaws classical feem ntau muaj ob kauj ruam: Ua ntej, methyl chloroformate reacts nrog triethylamine los tsim cov tshuaj nruab nrab methyl chloroformate ammonium ntsev; Tom qab ntawd, qhov nruab nrab no reacts nrog methyl carbamyl formate ntawm qhov kub thiab txias, thiab thaum kawg, cov khoom dawb crystallizes tawm.
3. Dab tsi yog qhov tseem ceeb tshaj plaws uas yuav tsum tau ua thaum sib xyaw thiab siv?
Lub ntsiab lus tseem ceeb yog ua haujlwm nruj me ntsis yam tsis muaj dej. Cov reagent no tsis tshua muaj rhiab heev rau cov dej noo thiab nws yooj yim rau hydrolysis thiab tsis ua haujlwm. Tag nrho cov tshuaj tiv thaiv yuav tsum tau ua nyob rau hauv kev tiv thaiv ntawm ib tug inert roj (xws li nitrogen los yog argon), siv anhydrous solvents thiab qhuav iav.

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