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CAS No. : | 594-65-0 | MDL No. : | MFCD00008009 |
Formula : | C2H2Cl3NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UPQQXPKAYZYUKO-UHFFFAOYSA-N |
M.W : | 162.40 | Pubchem ID : | 61144 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 29.06 |
TPSA : | 43.09 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.55 cm/s |
Log Po/w (iLOGP) : | 0.94 |
Log Po/w (XLOGP3) : | 1.04 |
Log Po/w (WLOGP) : | 0.84 |
Log Po/w (MLOGP) : | 0.49 |
Log Po/w (SILICOS-IT) : | 1.34 |
Consensus Log Po/w : | 0.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.44 |
Solubility : | 5.95 mg/ml ; 0.0366 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.54 |
Solubility : | 4.73 mg/ml ; 0.0292 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.36 |
Solubility : | 7.15 mg/ml ; 0.0441 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.43 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium carbonate | |
With hydrogenchloride | ||
With sulfuric acid |
With potassium carbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With perchloric acid; water; potassium hydrogen phthalate; potassium nitrate; potassium bromide at 25℃; for 1h; | ||
With bromine; trifluoroacetic acid; silver(l) oxide | ||
With dibromoisocyanuric acid In dichloromethane |
With bromine In acetic acid | ||
With acetyl hypobromite |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate | ||
With phosphorus pentaoxide | ||
With phosphorus pentaoxide |
With phosphorus pentoxide | ||
With oxalyl dichloride; dimethyl sulfoxide; triethylamine 1) CH2Cl2, -78 deg C, 15 min, 2) CH2Cl2, -78 deg C to RT; Yield given. Multistep reaction; | ||
With phosphorus pentoxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia | ||
With ethanol; ammonia |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sulfuric acid In nitrobenzene; chlorobenzene at 60℃; various temperatures, ΔG (excit.), ΔH (excit.), ΔS (excit.); | |
100% | With sulfuric acid at 25℃; | |
86% | With C19H23Cl2N6PRuS3*3ClH; water at 100℃; for 1h; Inert atmosphere; Schlenk technique; |
84% | With [RuCl2(η3:η3-2,7-dimethylocta-2,6-diene-1,8-diyl)(PMe2OH)] In water at 60℃; for 1h; Inert atmosphere; Sealed tube; | |
82% | With [Ru(OTf){η6:κ1(P)-PPh2-binaphthyl}{PPh2(OH)}][OTf] In water at 100℃; for 4h; Inert atmosphere; Sealed tube; | |
79% | With C14H30ClN3PRh; water at 100℃; for 0.5h; Inert atmosphere; Schlenk technique; | |
18% | With trifluorormethanesulfonic acid for 144h; Ambient temperature; | |
With hydrogenchloride anfangs unter Erwaermen; | ||
With dihydrogen peroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Trichloroethylene; ammonia at 30 - 40℃; | ||
With diethyl ether; ammonia | ||
With ammonium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: oxalyl dichloride; trichloroacetamide at 70℃; for 24h; Stage #2: at 100 - 140℃; for 25h; | A [0313] Step A: A reaction mixture of 2,2,2-trichloroacetamide (100 g, 616 mmol, 1.0 eq) in (COCl)2 (725 g, 5.71 mol, 500 mL, 9.28 eq) was heated to 70 °C for 24 hrs. The reaction mixture was concentrated under vacuum. To the mixture was added 1,2,4-trichlorobenzene (500 mL) and (COCl)2 (116 g, 914 mmol, 80 mL, 1.48 eq). The reaction mixture was stirred at 100 °C for 5 hours. The warmed to 125 °C for 15 hours. Then the mixture was warmed to 140 °C for 5 hours. The reaction mixture was distilled under water pump (72 °C- 76 °C fractions) to give 2,2,2- trichloroacetyl isocyanate (60 g, 319 mmol, 52 % yield) as a colourless oil which was used in the next step without further purification. |
In 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In benzene for 8h; Heating; | |
at 160℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With Diethyl phosphonate; triethylamine In benzene for 12h; Ambient temperature; | |
With triphenylphosphine In hexane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In benzene for 0.583333h; Heating; | |
In benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With trifluorormethanesulfonic acid In dichloromethane; cyclohexane for 18h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With boron trifluoride diethyl etherate at 40℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With sodium acetate In acetic acid for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium carbonate In acetonitrile for 480h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium carbonate In acetonitrile for 160h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With potassium carbonate In acetonitrile for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 31% 2: 24% | With potassium carbonate In acetonitrile for 40h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.2% | In acetic anhydride at 80℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49.3% | In acetic anhydride at 80℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With cyclohexene In dichloromethane at 15 - 20℃; for 1.5h; Irradiation; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 72% 2: 90% 3: 92% | With thiourea In acetonitrile Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With lead(II) bromide; aluminium In N,N-dimethyl-formamide for 6h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In dimethyl sulfoxide at 80 - 90℃; for 0.666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; 4-tert-Butylcatechol 1.) xylene, reflux, 18 h, 2.) THF, room temperature, 2.5 h; Yield given. Multistep reaction. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium carbonate In acetonitrile at 80℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With boron trifluoride diethyl etherate at 40℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate In dimethyl sulfoxide at 80 - 90℃; for 0.666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With boron trifluoride diethyl etherate at 40℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With potassium carbonate In dimethyl sulfoxide at 80 - 90℃; for 0.666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With diethylazodicarboxylate In diethyl ether; toluene at 0 - 20℃; for 12h; | |
62% | With diethylazodicarboxylate In tetrahydrofuran at 0 - 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With boron trifluoride diethyl etherate at 40℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate In dimethyl sulfoxide at 80 - 90℃; for 0.666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium carbonate In acetonitrile for 40h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium hydroxide In water 10 deg C, 20 min, then room temp., 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With boron trifluoride diethyl etherate at 40℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate In acetonitrile for 72h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With trithiazyl trichloride at 60℃; for 7h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With iron In N,N-dimethyl-formamide at 60℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 30% 2: 36% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 52% 2: 52% | With water at 140℃; for 6h; Sealed tube; | 2.3 General Reaction Procedure General procedure: In a typical reaction procedure 1 mmol benzonitrile and3 ml of H2O was taken in a sealed tube. About 80 mg ofcatalyst was added to this reaction mixture and stirred at140 °C on a oil bath for stipulated reaction time. Theprogress of the reaction was monitored by using thin layerchromatography. The products were identified by GC-MS(SHIMADZU-2010) analysis by separating the products ona DB-5 column. |
With hydrogenchloride at 20℃; for 96h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With diethylazodicarboxylate In diethyl ether; toluene at 0 - 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In diethyl ether at 0 - 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With chromium dichloride; hydrogen; magnesium bromide In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With chromium dichloride; hydrogen; magnesium bromide In tetrahydrofuran at 0℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With chromium dichloride; hydrogen; magnesium bromide In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With chromium dichloride; hydrogen; magnesium bromide In tetrahydrofuran at 0℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With N-iodo-succinimide In various solvent(s) at -75 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; urea; copper dichloride at 300℃; Formation of xenobiotics; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrafluoroboric acid In n-heptane; 1,2-dichloro-ethane at -15 - 20℃; Further byproducts given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: trichloroacetamide With phosphorus pentachloride In tetrachloromethane for 2h; Heating; Stage #2: With formic acid In tetrachloromethane for 0.5h; Further stages.; | ||
Stage #1: trichloroacetamide With phosphorus pentachloride In tetrachloromethane at 79.84℃; for 3h; Stage #2: With formic acid In tetrachloromethane for 2.5h; Cooling with ice; | 1 Synthesis of CCl3C(O)NHP(O)Cl2 CCl3C(O)NHP(O)Cl2 was synthesized from a reaction between phosphorous pentachloride (23 mmol) and 2,2,2-trichloroacetamide (23 mmol) in dry CCl4 (40 ml) at 353 K (3 h) and then treated with formic acid 85% (23 mmol) at ice-bath temperature (2.5 h). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethyl acetate | 3 2-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-3-methyl-5-(methylaminocarbonylaminosulfonyl)thiophene STR16 Example 3 2-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-3-methyl-5-(methylaminocarbonylaminosulfonyl)thiophene STR16 Preparation as in Example 1 from 2-[2-(5-chloro-2-methoxybenzoylamino)ethyl]-3-methyl-5-sulfamoylthiophene and trichloroacetamide. The crude product was purified by stirring in ethyl acetate at 30° C. M.p.: 185°-187° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6 2-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-4-(methyl-aminocarbonylaminosulfonyl)-5-methylthiophene STR19 Example 6 2-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-4-(methyl-aminocarbonylaminosulfonyl)-5-methylthiophene STR19 Analogously to Example 1 from 2-[2-(5-chloro-2-methoxybenzoylamino)ethyl]-5-methyl-4-sulfamoylthiophene and trichloroacetamide. M.p.: 198°-1990° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With trifluorormethanesulfonic acid In 1,2-dimethoxyethane; n-heptane at 7 - 25℃; for 19.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With tetrafluoroboric acid In dichloromethane; cyclohexane at -17 - 5℃; for 23.6667h; | 2.4 Step 4: Etherification FW mass volume mol equiv. Materials: Alcohol 3 466.58 6.73 kg 14.4 1.0 Imidate 4 402.55 9.33 kg active 23.2 1.6HBF4 (54 wt % 87.8 0.558 L 4.09 0.28in Et2O) cyclohexane 10 LCH2Cl2 9 L NaOH (2.0 N) 16 L 32 2.2 IPA 125 L Procedure: Charge the CH2Cl2 solution of the cyclohexanol 3 (containing 6.73 kg active 3+0.78 kg of related other alcohols and 6 L CH2Cl2, KF<250 ppm, equiv<1.2 mol % H2O) to a 100 L extractor. Charge the imidate solution (850 g/L in cyclohexane, 11 L, containing 2 L cyclohexane) followed by additional cyclohexane (8.0 L). The mixture turns cloudy due to 3 oiling out. Add more CH2Cl2 (2 L) to dissolve the oil. Cool to -17° C. (oiling out at 0° C.) and add more CH2CL2 (1.3 L) to dissolve the oil. The KF at this point should be <110 ppm (<1.5 mol % water). Add 0.17 equiv of HBF4 (0.339 L) in one portion, resulting in temperature rising to -16° C. The slightly cloudy mixture is aged at -16° C. It turns clear in 40 min and a slurry starts to form and thickens as the reaction proceeds to generate poorly soluble trichloroacetamide A. After aging at -16° C. for 18 hours, LC assay reveals 82% conv and a 5/5a ratio of 6. For slightly higher conversion, 0.11 equiv more HBF4 (0.219 L) is added following by aging at -16° C. for 4 h. The reaction is then warmed to 5° C. and aged for 1 h before being quenched with NaOH (2 N, 16 L). The exotherm brings the temperature to 18° C. After aging at rt for 15 min, the layers are allowed to settle. The bottom aqueous layer (18 L) is cut away and the organic layer is washed with 18 L of water. The cloudy bottom organic layer is collected (assay yield of 5: 74%), concentrated to 20 L, and flushed with IPA (90 L) while keeping batch temperature at 40° C. and volume at 50-60 L to enable stirring as the product crystallizes out. A final volume of 70 L is reached and the thick slurry is aged at rt until mother liquor shows<11 g/L loss (5/5a<0.55). The product is then filtered, washed with IPA (35 L), and dried. 7.07 kg, 98 A %, 96 wt %, 6.82 kg corrected, 67% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: tert-Butyl 2,2,2-trichloroacetimidate; Koshlands reagent I In dichloromethane; cyclohexane for 4.5h; Stage #2: With boron trifluoride diethyl etherate In cyclohexane; water-d2 Stage #3: With water; sodium hydrogencarbonate In dichloromethane; cyclohexane for 1h; | 1 2-0C and stirring for an additional hour, the resulting solid was collected by filtration, washed with cold, fresh hexane, suctioned dry and vacuum dried. The yield was 13.2 g, 55% based on 2-hydroxy-5-ϖitrobenzyl bromide. CaIc C 45.85, H 4.90, N 4.86, Br 27.73. Found C 45.39. H 5.07, N 4.94, Br 27.66. 1H nmr (300MHz CDCI3) δ (ppm). 1.58 (s, 9H), 4 48 (s. 2H), 7.10 (d, JH = 9Hz, 1 H), 8.11 (dd, J=9Hz, J=2.7Hz, 1 H), 8.22 (d, J=2.7Hz, 1 H). 13C (75.45 MHz, CDCI3) δ (ppm). 28.92, 81.59, 116.86, 125 07. 126 34, 129.98, 140 69, 159 97 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With KO(t)Bu In dichloromethane 2 equiv. KO(t)Bu, warming from -20°C to room temp.; | |
96% | With KOC(CH3)3 In dichloromethane under Ar; KOC(CH3)3 was added to a mixt. of the triarylbismuth dichloride, the amide and CH2Cl2 at -50°C, the mixt. was allowed to warm gradually to 25°C with stirring; the insol. solid was filtered through Celite, the filtrate was concd. under vac., the oily residue was crystd. from CH2Cl2/hexane; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With KO(t)Bu In dichloromethane 2 equiv. KO(t)Bu, warming from -20°C to room temp.; | |
77% | With KOC(CH3)3 In dichloromethane under Ar; KOC(CH3)3 was added to a mixt. of the triarylbismuth dichloride, the amide and CH2Cl2 at -50°C, the mixt. was allowed to warm gradually to 25°C with stirring; the insol. solid was filtered through Celite, the filtrate was concd. under vac., the oily residue was crystd. from CH2Cl2/hexane; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With CH3CH2O2CNNCO2CH2CH3 In diethyl ether; toluene under Ar; a soln. of diethyl azodicarboxylate in toluene was added to a mixt. of tris(2,4,6-trimethylphenyl)stibane, the amide and diethyl etherat 0°C, the mixt. was stirred for 30 h; the volatiles were removed in vac., the oily residue was washed with diethyl ether and THF and crystd. from CH2Cl2/hexane; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 0 - 20℃; | 15 Example 15: Benzyloxy protection of (S)-3-Methyl-2-(2-nitro-ethyl)-butan-1-ol; 1.0 g (6.2 mmol) of S)-3-Methyl-2-(2-nitro-ethyl)-butan-1-ol is dissolved in 15 ml of dichloromethane at room temperature and 2.35 g (6.8 mmol) of benzyl (2,2,2)-trichloro acetimidate and 50 mg (0.33 mmol) trifluoromethanesulfonic acid as catalyst is added at 0 0C under stirring. A white precipitate of trichloroacetamide is formed after a short periode of time. The reaction mixture is stirred at room temperature over night and after complete conversion (TLC) the reaction mixture is filtered to remove precipitated trichloro acetamide. The filtrate is washed with aqu. saturated bicarbonate solution, with water and dried over Na2SO4. The solvent is evaporated in vacuum to give the crude product. The crude product was chromatographed over silicagel with ethyl acetate/ heptane (1 :4) to give the product as an oil.1H-NMR: (400 MHz, CDCI3); δH (ppm) δ = 0.83 (6H, d, 2 x CH3), 1.43-1.52 (1 H, brm, -CH), 1.62-1.72 (1 H, m, -CH), 1.88- 1.98(1 H, m, -CH), 2.02-2.12 (1 H, m, -CH), 3.27-3.33 (1 H, dd, -OCH), 3.38-3.44 (1 H, dd, -OCH), 4.32-4.48 (4H, comp. m, -CH2-NO2, & -OCH2-Ph), 7.20-7.36 (5H, brm, arom.-H).MS: [M + H] = 252IR: (FTIR-Microscopy in transmission)2961 , 2931 , 2875, 1552 (-NO2) , 1384 (-NO2), 1095 (C-O), 739, 699 [cm-1] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroborane diethyl ether In dichloromethane; cyclohexane | 1 2-t-Butoxy-5-nitrobenzyl bromide (1) 2-t-Butoxy-5-nitrobenzyl bromide (1) A suspension of 2-hydroxy-5-nitrobenzylbromide, 19.4 g 0.0836 mole, cyclohexane, 334 mL, and dichloromethane, 167 mL, was stirred under nitrogen. To this suspension was added a solution of t-butyl trichloroacetimidate, 73.08 g 0.334 mole, in cyclohexane, 669 mL, dropwise over 3.5 hours. The mixture was stirred for one hour after completion of the addition and boron trifluoride etherate, 200 μL, was added. The mixture was allowed to stir overnight. A large amount of precipitate, trichloroacetamide, formed. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With boron trifluoride diethyl etherate In dichloromethane for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With camphor-10-sulfonic acid In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In pyridine; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetic anhydride | 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose1 8 Route 1: The raw reaction product 9 obtained is dissolved in a pyridine/acetic anhydride mixture (1/1, 50 mL) at 0° C. and the reaction mixture is stirred overnight at RT. After verifying, by TLC (DCM/EtOAc, 9/1), the appearance of two new compounds (Rf=0.45 and 0.2), the reaction mixture is concentrated in a rotary evaporator and then coevaporated with Tol (3*100 mL) and DCM (3*100 mL). The residue is dried with a vane pump to give the expected derivative in the form of a solid corresponding to a mixture of α/β anomers. The solid obtained is purified by silica gel chromatography (DCM/EtOAc, 97/3→9/1) to give, in the order of elution, the desired monosaccharide 8α (6.6 g, 57%) and then the stereoisomer 8β (3.5 g, 31%). The two anomers 8α and 8β (65/35) are isolated as a white solid (10.1 g, 88%). Route 2: Glucosamine hydrochloride 7 is added in portions (5 g, 13.1 mmol) to a solution of DCM (40 mL) and pyridine (5.2 mL, 65.3 mmol, 5 eq.). The reaction mixture is put on an ice bath and then trichloroacetyl chloride (4.1 mL, 36.0 mmol, 2.8 eq.) is added dropwise. After stirring for 15 min at 0° C., the reaction mixture is stirred for 30 min at RT. The reaction is monitored by TLC (DCM/EtOAc, 9/1), and the appearance of a less polar product (Rf=0.2) is observed. The reaction mixture is taken up in H2O (20 mL) and the aqueous phase is extracted with DCM (3*30 mL). The organic phases are combined and washed with a solution of 5% NaHCO3 (3*50 mL), with H2O (3*50 mL) and then dried over Na2SO4 and concentrated in a rotary evaporator to give a white solid (6.3 g, 98%) corresponding to the anomer 8β. 8α: Rf=0.45 (DCM/EtOAc, 9/1). 1H NMR (CDCl3), δ6.83 (d, 1H, JNH,2=8.3 Hz, NHα), 6.29 (d, 1H, J1,2=3.7 Hz, H-1), 5.34 (pt, 1H, J2,3=9.6 Hz, H-3), 5.23 (pt, 1H, J3,4=9.8 Hz, H-4), 4.35-4.25 (m, 2H, H-2, H-6a), 4.07-4.01 (m, 2H, H-5, H-6b), 2.18, 2.08, 2.05 (3s, 12H, HAc). 13C NMR (CDCl3), δ172.0, 171.0, 169.4, 168.7 (4C, CAc), 162.3 (CNTCA), 92.1 (CCl3), 89.9 (C-1, 1JCH=179.2 Hz), 70.4 (C-5), 70.2 (C-3), 67.4 (C-4), 61.7 (C-6), 53.7 (C-2), 21.1, 21.0, 20.9, 20.8 (4C, CAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide at 0 - 25℃; Inert atmosphere; Darkness; optical yield given as %de; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | Stage #1: trichloroacetamide With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: (S)-proline-N-carboxyanhydride In tetrahydrofuran at -78 - 20℃; Stage #3: With water; ammonium chloride In ethyl acetate | 15 D.A. Berges, W.E. DeWolf, G.L. Dunn, S.F. Grappel, D.J. Newman, J.J. Taggart and C. Gilvarg, . J. Med. Chem., 29 (1986), pp. 89-95 General procedure for the synthesis of 1 and 2. General procedure: Proline N-carboxyanhydride was synthesized starting from l-proline according to the published method.refPreviewPlaceHolder14 The solution was used immediately. A solution of the corresponding amide (6.8 mmol) in THF (50 mL) was cooled to -78 °C, BuLi (8.5 mL, 13.6 mmol) was added, and the mixture was stirred for 10 min. A solution of proline N-carboxyanhydride (6.8 mmol) in THF (10 mL) was added, and the reaction was completed by stirring at -78 °C for 1 h. The mixture was warmed to room temperature, and the solvent removed by evaporation. To the mixture 50 mL ethyl acetate and a saturated solution of NH4Cl (8 mL) were added. The layers were separated, and the aqueous layer was extracted with EtOAc (2 × 50 mL). The combined organic layers were dried with Na2SO4 and concentrated in vacuo. The product was purified by flash silica gel chromatography (hexane/EtOAc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In tetrahydrofuran | 4 2,2,2-Tris-N-Methylimidazole-acetic acid amide (Tris-CONH2) Example 4 2,2,2-Tris-N-Methylimidazole-acetic acid amide (Tris-CONH2) 4.875 g (30 mmol) 2,2,2-Trichloroacetamide were dissolved in 40 ml THF and 7.2 ml (90 mmol) N-methylimidazole added under stirring. Stirring was continued overnight and then the solvent removed under vacuum. Yield: 12.03 g; 98%. 1H NMR (DMSO, ppm): δ: 3.63 (s, 9H, CH3), 6.89 (s, 3H, H5), 7.09 (s, 3H, H4), 7.56 (s, 3H, H2), 8.46 (s, 1H, NH2), 8.59 (s, 1H, NH2) 13C NMR (DMSO, ppm): δ: 32.77 (CH3), 93.20 (C), 120.52 (C5), 128.41 (C4), 137.92 (C2), 163.09 (C=O) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.01 g | Stage #1: trichloroacetamide With potassium hydroxide In toluene at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: diethyl chlorophosphate In toluene at 0 - 20℃; for 3h; Inert atmosphere; Stage #3: With hydrogenchloride In water Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triphenylphosphine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Stage #1: farnesol With phosphorus tribromide In diethyl ether at 0℃; for 1h; Stage #2: trichloroacetamide With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 27h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With [Cu(dimethyl (2,2'-bipyridine)-4,4'-dicarboxylato)F<SUB>2</SUB>]<SUB>2</SUB>*2H<SUB>2</SUB>O; [Ag(2,9-dimethyl-1,10-phenanthroline)(MeCN)]BF4 In acetonitrile at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | at 150℃; for 24h; Sealed tube; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 22h; | 2 Example 2: Synthesis of 2.2.2-trichloro-/V-((3-oxoquinuclidin-2- vQmethvQacetamide 2-Methylenequinuclidin-3-one (150 mg, 1.09 mmol) was dissolved in DMF (3 ml_) and K2CO3 (151 mg, 1.09 mmol) was added followed by addition of trichloroacetamide (178 mg, 1.09 mmol). The reaction mixture was stirred at room temperature for 20 hours and at 50°C for 2 hours to give the desired product, in addition to unreacted starting material. The solids were filtered off and the filtrate was concentrated. The crude material was purified by preparative HPLC (XBridge C18; 50 mM NH4HC03/MeCN; 9:1 to 6:4) to give the title compound (140 mg, 43%). MS ESI+ (m/z): 299, 301 , 303 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With ammonium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; acetonitrile at 20℃; for 0.5h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; potassium carbonate; copper(l) chloride In dichloromethane at 50℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; potassium carbonate; copper(l) chloride In dichloromethane at 50℃; for 12h; Inert atmosphere; |
Tags: 594-65-0 synthesis path| 594-65-0 SDS| 594-65-0 COA| 594-65-0 purity| 594-65-0 application| 594-65-0 NMR| 594-65-0 COA| 594-65-0 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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