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CAS No. : | 2198-53-0 | MDL No. : | MFCD00008675 |
Formula : | C10H13NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NRPTXWYBRKRZES-UHFFFAOYSA-N |
M.W : | 163.22 | Pubchem ID : | 16616 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 50.69 |
TPSA : | 29.1 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.54 cm/s |
Log Po/w (iLOGP) : | 2.0 |
Log Po/w (XLOGP3) : | 1.07 |
Log Po/w (WLOGP) : | 2.07 |
Log Po/w (MLOGP) : | 2.15 |
Log Po/w (SILICOS-IT) : | 2.32 |
Consensus Log Po/w : | 1.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.76 |
Solubility : | 2.81 mg/ml ; 0.0172 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.27 |
Solubility : | 8.71 mg/ml ; 0.0534 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.55 |
Solubility : | 0.0461 mg/ml ; 0.000282 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | 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 |
---|---|---|
84% | Stage #1: With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.5 h; Stage #2: With cerium(III) chloride In tetrahydrofuran; dichloromethane at -78℃; for 2 h; Stage #3: With hydrogenchloride In ethyl acetate |
General procedure: Tf2O (185μL, 1.1mmol) was added dropwise to a cooled (0°C) solution of amide (1.0mmol) and 2-fluoropyridine (103μL, 1.2mmol) in dichloromethane (4mL). After stirring at 0°C for 30min, the mixture was cannulated to a freshly prepared organocerium reagent/complex (3.0mmol) in THF (15mL) at −78°C and stirred for 2h. Aqueous HCl solution (3mol/L, 5mL) was added to quench the reaction and the mixture was allowed to warm to r.t. and stirred for 2h. Ammonium hydroxide solution (25percent, 5mL) was then added to the mixture. The organic layer was separated and the aqueous phase was extracted with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25percent, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With sodium tungstate; sodium perborate; sulfuric acid; acetic anhydride; potassium bromide In acetic acid for 1h; Ambient temperature; | |
With chloroform; bromine; iron |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 44% 2: 11 % Spectr. | With peracetic acid; sulfuric acid; potassium bromide In acetic anhydride; acetic acid for 1h; | |
With bromine; acetic acid | ||
With acetic acid Bromieren; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With potassium permanganate In water for 1.5h; Heating; | |
With potassium permanganate; water; magnesium sulfate | ||
With potassium permanganate |
With permanganate(VII) ion |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; nitric acid man verseift das Acetylderivat mit konz.Salzsaeure; | ||
With sulfuric acid; nitric acid at 0℃; man verseift das Acetylderivat mit konz.Salzsaeure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With benzyltrimethylazanium tetrachloro-λ3-iodanuide; acetic acid at 70℃; for 20h; | |
With chlorine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sulfuric acid; nitric acid; acetic acid at 0 - 20℃; for 1h; | 10 N-(2,6-dimethyl-3-nitro-phenyl)acetamide N-(2,6-dimethylphenyl)acetamide (10 g, 60 mmol, 1.0 eq) was dissolved in a mixture of H2S04 (40 mL) and acetic acid (20 mL) at 0°C. A mixture of HN03 (10 mL) and H2S04 (8 mL) was added drop wise with stirring. The reaction was allowed to warm to room temperature and stirred for a further lh. The reaction was quenched by pouring into ice water, and the solid that formed collected by filtration to give the title compound as a yellow solid (12 g, 94 %).LC-MS: 209.1 [M+H]1H MR (400 MHz, DMSO-d6) ? 9.58 (s, 1H), 7.75 (d, J = 8.4 Hz, 1H), 7.33 (d, J = 8.4 Hz, 1H), 2.23 (s, 3H), 2.23 (s, 3H), 2.09 (s, 3H) |
91% | With sulfuric acid; nitric acid In acetic acid at 0 - 22℃; for 1h; | 3E.A EXAMPLE 3E; Synthesis of 2-carbomethoxy-6,8-dimethyl-4-hydroxy-7-methoxyquinoline (E8); Step A The amide El (5.0 g, 30.63 MMOL) was dissolved in a mixture of acetic acid (5 mL) and sulfuric acid (10 mL) and cooled to 0°C. A mixture of nitric acid (70%, 3 mL) and sulfuric acid (2 mL) was added dropwise after which the solution was warmed to R. T. and stirred for 1 h. The reaction mixture was then poured onto crushed ice and filtered (after the ice had melted but the solution was still cold) to yield the desired compound E2 (5.8 g, 91%) which was carried forward to the next reaction without further purification. MS ES+-209. 0, ES- = 206. 9. (REF : GIUMANINI, A. G. ; Verardo, G.; Polana, M. J. PRAK. Chem. 1988, 181). |
80% | With nitric acid In sulfuric acid; acetic acid for 1h; Ambient temperature; |
With nitric acid; dinitrogen tetraoxide at -15℃; | ||
With nitric acid | ||
35.5 g (92%) | With sulfuric acid; nitric acid; acetic acid | 1 Preparation of N-acetyl-2,6-dimethyl-3-nitroaniline Preparation of N-acetyl-2,6-dimethyl-3-nitroaniline To a mixture of 30.1 g of N-acetyl-2,6-xylidine (0.18 mole) and 40 ml of acetic acid (0.70 mole) was added gradually 80 ml of concentrated sulfuric acid (0.50 mole) with stirring under ice-cooling. Then, to the mixture was added slowly 10 ml of fuming nitric acid (0.24 mole) in a manner such that the temperature of the reaction mixture did not exceed 10° C. The reaction mixture was returned to room temperature and, after stirring for 2 hours, poured onto ice. The resulting crystalline precipitate was collected by filtration and recrystallized from ethanol to give 35.5 g (92%) of the title compound (m.p. 171°-173° C.; pale yellow needles). IR(cm-1;KBr): 1650 (--CONH--) 1520, 1350 (--NO2). |
With sulfuric acid; nitric acid | 7.A This compound was prepared using procedures described in EP 153855. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sulfuric acid; nitric acid at 0℃; for 24h; | |
With sulfuric acid; nitric acid | ||
With sulfuric acid; nitric acid at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogenchloride; sodium nitrite In dichloromethane at 20 - 25℃; for 0.25h; | |
With acetic acid Einleiten von nitrosen Gasen; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | ||
94% | With In(OSO2CF3)3 In acetonitrile at 20℃; | |
92% | With sulfonic acid-functionalized hyper-cross-linked poly(2-naphthol) In neat (no solvent) at 25℃; for 0.25h; Green chemistry; chemoselective reaction; | 2.3 General Procedure forAcylation Reaction General procedure: To a 10mL reaction flask phenol/alcohol/thiol/amine/aldehyde(1mmol), acetic anhydride (1mmol) and p2NPh-OSO3H(10mg) as a catalyst was added and the resulting mixturestirred at 25°C. The progress of the reaction was checkedusing thin layer chromatography (TLC). After completion,ethyl acetate (EA) was added and the catalyst was separatedfrom the reaction mixture by straightforward filtration. Theseparated catalyst was cleaned with EA (10mL) and then driedin an oven for 2h and reused for further reaction. The reactionmixture was evaporated under reduced pressure to get theproducts which were characterized by 1H and 13C NMR spectroscopy.All of the obtained products are renowned withinthe literature. |
91% | With N,N,N-trimethyl-2-(sulfooxy)ethanaminium chloride In neat (no solvent) at 20℃; for 0.333333h; Milling; Green chemistry; | General procedure for the preparation of compounds (1-21). General procedure: A mixture of amine (1 mmol), acetic anhydride (1 mmol) and 3.5 mol% SCIL was systematically mixed in a mortar followed by grinding at room temperature. The sticky mixture got solidified within 10-20 min. The mixture was powdered till the completion of reaction as indicated by TLC. The product was dissolved in ethyl acetate to recover the insoluble catalyst. The filtered catalyst was dried at 60oC under vaccum for 1 h after thoroughly washing with ethyl acetate. The recovered SCIL was recycled in the model reaction for six times to check its catalytic efficiency. The products were recrystallized from hot methanol. |
89% | at 20℃; | |
78% | for 0.0333333h; | |
74% | at 0 - 20℃; for 1h; | 10 N-(2,6-dimethylphenyl)acetamide 2,6-dimethylaniline (10 g, 82.5 mmol, 1.0 eq) was added to acetic anhydride (100 mL) at 0°C. The reaction mixture was then warmed to room temperature and stirred for lh. The reaction was poured into ice water and the precipitate that formed collected by filtration to give the title compound as a yellow solid (10 g, 74 %). |
With pyridine for 2h; Heating; | ||
With hydrogenchloride | ||
With triethylamine In dichloromethane at 20℃; for 10h; Cooling with ice; | 25.1 1st step: N - (2, 6 - dimethyl-phenyl) acetamide (25 a) N - (2, 6 - dimethylphenyl) acetamideThe 2, 6 - dimethylaniline 1 a (10 g, 0.083 µM), triethylamine (16.69 g, 0 . 165 µM) are added to a reaction in the bottle, by adding dichloromethane (100 ml), ice bath, stirring the dripping compound is added acetic anhydride (12.64 g, 0 . 124 µM), canada finishes, stirring at room temperature for 10 hours. The reaction liquid is added to the saturated salt water (100 ml), stirring of the liquid, aqueous phase for dichloromethane (50 ml × 2) extraction, the combined organic phase, and with anhydrous sodium sulfate drying, filtering, the filtrate to dryness, the residue by adding petroleum ether (50 ml) stirring 30 minutes, filtered, the filter cake is petroleum ether (50 ml × 2) washing, to obtain white solid compound 25 a (crude product 13 g, yield: 96.5%), directly used in the next step. | |
In ethanol; water at 70℃; | A general procedure for reductive acetylation of nitroarenes General procedure: In a round-bottom flask (25 mL), a solution of nitrobenzene (0.123 g, 1 mmol) in H2O-EtOH (1.5:0.5 mL) was prepared. Magnetically, nanoparticles of NiFe2O4(at)Cu (0.15 g) were added, and the resulting mixture was stirred for 5 min. Afterward,NaBH4 (0.094 g, 2.5 mmol) was added and the resulting mixture was continued to stirring for 1 min at 70 °C. After reduction of nitrobenzene to aniline (monitored by TLC), Ac2O (0.204 g, 2 mmol) was added and the resulting mixture was stirred for 1 min at 70 °C. The nanocatalyst was separated by an external magnet, and the mixture was extracted with EtOAc (3 × 5 mL). The organic layer was dried over anhydrous Na2SO4. Evaporation of the solvent affords the pure acetanilide in 95% yield (0.128 g, Table 3,entry 1). | |
With acetic acid at 20 - 80℃; for 2.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 3% 2: 16% 3: 28% | With sodium acetate In acetonitrile for 1h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With Lawessons reagent In benzene for 1h; Heating; | |
Multi-step reaction with 2 steps 1: 92 percent / HCl, NaNO2 / CH2Cl2 / 0.25 h / 20 - 25 °C 2: 100 percent / 2,4-bis-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide / 1,2-dimethoxy-ethane / 24 h / Ambient temperature | ||
With Lawessons reagent In toluene at 120℃; for 2h; | 4.1 First, 8.1 g of 2,6-dimethylacetanilide and 100 mL of toluene were put in a 200 mL three-neck flask, and stirred to be mixed. Then, 10 g of 2,4-bis(4-methoxyphenyl)-l,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) was added to this mixture, and heated and stirred at 120 °C for 2 hours to be reacted. The reaction solution was concentrated to give an oily substance. This oily substance was purified by silica gel column chromatography. As a developing solvent, hexanerethyl acetate = 5:1 was used. The resulting fraction was concentrated, so that N-(2,6-dimethylphenyl)thioacetanilide was prepared as a brown oily substance. The prepared oily substance, 3.4 g of sodium ethoxide, and 40 mL of ethanol were put in a 100 mL three-neck flask, and stirred at room temperature for 1 hour. Then, 4.0 mL of iodoethane was added to this mixture, and heated and stirred at 60 °C for 5 hours to be reacted. After the reaction, ethanol was distilled off under a reduced pressure to give a brown oily substance. This oily substance was dissolved in dichloromethane, and washed with water and then a saturated aqueous solution of sodium hydrogen carbonate. After the washing, anhydrous magnesium sulfate was added to the resulting organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated, so that N-[l-(ethylsulfanyl)ethylidene]-2,6-dimethylaniline was prepared (a brown solid, crude yield: 76 %). The synthetic scheme of Step 1 is shown by (a-4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water-d2 at 120℃; for 480h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorosulfonic acid; sodium hydroxide | ||
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 1.42 h / 5 - 40 °C 2: hydrogenchloride; water / 1 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorosulfonic acid at 5 - 40℃; for 1.41667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With aluminium trichloride In benzene for 3h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With pyridine for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With sulfuric acid at 80℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.1% | With palladium diacetate In acetic acid at 100℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In chloroform for 0.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid at 70℃; for 24h; | |
90% | With peracetic acid; sulfuric acid; hydrogen iodide In acetic anhydride; acetic acid | |
72% | With sodium tungstate; sulfuric acid; dihydrogen peroxide; acetic acid; potassium iodide at 50℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride In nitrobenzene at 100℃; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In ethyl acetate at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In ethyl acetate at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 58 percent / n-BuLi / tetrahydrofuran; hexane / Heating 2.1: AcOH / 1 h / 50 °C 2.2: 94 percent / Ag2CO3 on Celite / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 58 percent / n-BuLi / tetrahydrofuran; hexane / Heating 2.1: AcOH / 1 h / 50 °C 2.2: 94 percent / Ag2CO3 on Celite / 4 h / 20 °C 3.1: 84 percent / aq. NaOH / methanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: AlCl3 / nitrobenzene / 100 °C 2: Fe,NH4Cl / ethanol; H2O / Heating 3: conc. aq. HCl / ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: AlCl3 / nitrobenzene / 100 °C 2: Fe,NH4Cl / ethanol; H2O / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ClSO3H / 1.42 h / 5 - 40 °C 2: aq. ammonia 3: HCl / 1 h / Heating | ||
Multi-step reaction with 2 steps 1: 1.) ClSO3H; 2.) NaOH 2: H2SO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80 percent / 65percent HNO3 / acetic acid; H2SO4 / 1 h / Ambient temperature 2: 80 percent / 70percent aq. H2SO4 / 115 h / 120 °C | ||
Multi-step reaction with 2 steps 1: nitric acid / <0 2: Verseifung |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 80 percent / 65percent HNO3 / acetic acid; H2SO4 / 1 h / Ambient temperature 2: 80 percent / 70percent aq. H2SO4 / 115 h / 120 °C 3: 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 51 percent / H2O2 / aq. acetic acid / Heating 2: 32 percent / H2SO4 / 1 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: D2O / Pd/C / 480 h / 120 °C 2: 1.) ClSO3H; 2.) NaOH 3: H2SO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) ClSO3H; 2.) NaOH 2: H2SO4 3: 1.) NaOH; 2.) m-chlorobenzoic acid / methanol | ||
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 1.42 h / 5 - 40 °C 2: hydrogenchloride; water / 1 h / Reflux 3: 3-chloro-benzenecarboperoxoic acid / methanol / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: D2O / Pd/C / 480 h / 120 °C 2: 1.) ClSO3H; 2.) NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: D2O / Pd/C / 480 h / 120 °C 2: 1.) ClSO3H; 2.) NaOH 3: H2SO4 4: 1.) NaOH; 2.) m-chlorobenzoic acid / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzene 2: N2H4*H2O / Raney-Ni / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With triethylamine In dichloromethane at 0℃; | 1 Dimethyl aniline (100 g, 82.5 mmoles; Scheme 1) was dissolved in 400 mL of dichloromethane and cooled to 0° C. To this solution was added dropwise acetyl chloride (71 mL, 1 mole) followed by a 200 mL solution of triethyl amine (140 mL, 1 mole). This solution was stirred until complete. Filter off the solid and pour the filtrate into brine, extract twice with dichloromethane, dry filter and concentrate to give 127.3 g (95% yield) of the acetylated amine as a tan solid. |
74% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 13.1 Step 1. Compound 3 Compound 1 (6.0g, 49.5mmol, 1.0eq) and diisopropylethylamine (12.8g, 99.0mmol, 2.0eq) were added to dichloromethane (100mL), and the above solution was cooled to At 0°C, compound 2 (5.83 g, 74.3 mmol, 1.5 eq) was slowly added dropwise to the reaction solution, and the reaction solution was reacted at room temperature for 2 hours under nitrogen protection.The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1:1) to obtain white solid 3 (6.0 g, yield 74%). |
In dichloromethane |
In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.1 g (91%) | With acetic anhydride; acetic acid | 1 Preparation of N-acetyl-2,6-xylidine Preparation of N-acetyl-2,6-xylidine To 25 ml of 2,6-xylidine (0.20 mole) was added slowly a mixture of 25 ml of acetic anhydride (0.26 mole) and 25 ml of acetic acid (0.44 mole) under stirring at room temperature. The mixture was stirred for 30 minutes at room temperature and, then, diluted with water. The crystalline precipitate was collected by filtration to give 30.1 g (91%) of the title compound (m.p. 182°-184° C.; colorless needles). |
In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In melt byproducts: acetic acid; heated for 2 h at 200°C under Ar, the acetic acid formed during the reaction is removed under vac. at room temp., this cycle of heating, cooling and evacuation is repeated several times; sublimed at 100°C, the solid is washed (ether), recrystd. (CH2Cl2); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-LiBu In tetrahydrofuran under N2; a solution of the organic compound (THF) was treated with n-LiBu (hexane); the chromium compound was added; stirred for 16 h at room temperature; filtered; slowly evaporated to dryness using an Ar-flow; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene | S.4.1 Step 1: Step 1: Synthesis of N-[1-(ethylsulfanypethylidene]-2,6-dimethylaniline First, 8.1 g of 2,6-dimethylacetanilide and 100 mL of toluene were put in a 200 mL three-neck flask, and stirred to be mixed. Then, 10 g of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson's reagent) was added to this mixture, and heated and stirred at 120° C. for 2 hours to be reacted. The reaction solution was concentrated to give an oily substance. This oily substance was purified by silica gel column chromatography. As a developing solvent, hexane:ethyl acetate=5:1 was used. The resulting fraction was concentrated, so that N-(2,6-dimethylphenyl)thioacetanilide was prepared as a brown oily substance. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: Lawessons reagent / toluene / 2 h / 120 °C 2.1: sodium ethanolate / ethanol / 1 h / 20 °C 2.2: 5 h / 60 °C 3.1: hydrazine hydrate / butan-1-ol / 5 h / 80 °C 3.2: 22 h / 130 °C 3.3: 11 h / 80 - 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: Lawessons reagent / toluene / 2 h / 120 °C 2.1: sodium ethanolate / ethanol / 1 h / 20 °C 2.2: 5 h / 60 °C 3.1: butan-1-ol / 17 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: Lawessons reagent / toluene / 2 h / 120 °C 2.1: sodium ethanolate / ethanol / 1 h / 20 °C 2.2: 5 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphorus pentachloride Heating; Neat (no solvent); | ||
With bis(trichloromethyl) carbonate | ||
With bis(trichloromethyl) carbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorosulfonic acid at 5 - 40℃; for 1.41667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With aluminum (III) chloride; triethylamine at 25℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With trifluorormethanesulfonic acid; iodine In 5,5-dimethyl-1,3-cyclohexadiene at 110℃; for 24h; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With manganese(III) fluoride; palladium diacetate; acetic acid In 2,2,2-trifluoroethanol; water at 40℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: sulphapyridine With hydrogenchloride In methanol; acetonitrile at 0℃; for 0.25h; Stage #2: With isopentyl nitrite In methanol; acetonitrile at 0 - 20℃; Inert atmosphere; Stage #3: N-(2,6-dimethylphenyl)acetamide With potassium carbonate In methanol; acetonitrile at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: Tf2O (185muL, 1.1mmol) was added dropwise to a cooled (0C) solution of amide (1.0mmol) and 2-fluoropyridine (103muL, 1.2mmol) in dichloromethane (4mL). After stirring at 0C for 30min, the mixture was cannulated to a freshly prepared organocerium reagent/complex (3.0mmol) in THF (15mL) at -78C and stirred for 2h. Aqueous HCl solution (3mol/L, 5mL) was added to quench the reaction and the mixture was allowed to warm to r.t. and stirred for 2h. Ammonium hydroxide solution (25%, 5mL) was then added to the mixture. The organic layer was separated and the aqueous phase was extracted with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25%, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | at 119 - 129℃; for 0.833333h; Reflux; | 3 General procedure: In the is provided with a stirrer, thermometer, reflux condenser, dropping funnel in the reaction container, adding 2,6-dimethyl aniline (2) 1.1mol, control the stirring speed 140rpm, dropping phenylacetaldehydes (3) 1.53mol, control the temperature of the solution in 119 °C, after the completion of the dropping, the temperature of the solution elevated to 129 °C, make it totally dissolve, reaction 50 min later, by adding 400 ml mass fraction is 35% sodium chloride solution, separating solid, reducing the temperature of the solution to 38 °C, filtering, potassium nitrate solution until the pH is 9, is dehydrated by anhydrous sodium sulfate, the mass fraction is 98% recrystallization in ether, may be 2,6-dimethyl- monoacetylaniline 163.16g, yield 91%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With 2,6-dimethylpyridine; dmap; di-<i>tert</i>-butyl dicarbonate In acetonitrile at 20 - 28℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.5% | Stage #1: N-(2,6-dimethylphenyl)acetamide With trichlorophosphate In toluene at 20℃; for 2h; Stage #2: piperidine In toluene for 12h; Reflux; | 25.2 2nd step: (E)- 2, 6 - dimethyl - N - (1 - (piperidine -1 - yl) ethylidene) aniline (25 b) (E)- 2, 6 - dimethyl - N - (1 - (piperidin - 1 - yl) ethylidene) anilineThe compound 25 a (3 g, 0.018 µM) dissolved in toluene (30 ml) in, at room temperature by the addition of phosphorus oxychloride (2.825 g, 0 . 018 µM) stirring at room temperature for 2 hours. Then the piperidine (1.564 g, 0 . 018 µM) dissolved in toluene (30 ml) is added in the reaction solution in and drop, heating reflux for 12 hours. The reaction fluid evaporation, adding ethyl acetate (50 ml) and saturated sodium bicarbonate solution (50 ml) stirring of the liquid, aqueous phase is used which ethyl acetate (50 ml × 2) extraction, the combined organic phase and saturated salt water (100 ml × 3) washing, the organic phase is dried with anhydrous sodium sulfate, filtered and evaporation to dryness, the residue is silica gel column chromatography (CH2Cl2/MeOH=30/1 - 15/1) separation and purification, to obtain white solid compound 25 b (0.8 g, yield 18.5%), used directly for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15.5% | Stage #1: N-(2,6-dimethylphenyl)acetamide With trichlorophosphate In toluene at 20℃; for 2h; Stage #2: cyclohexylamine In toluene for 12h; Reflux; | 31.1 1st step: (E)- N' - cyclohexyl - N - (2, 6 - dimethyl-phenyl) acetamidine (31 b) (E)- N ' - cyclohexyl - N - (2, 6 - dimethylphenyl) acetimidamideThe N - (2, 6 - dimethyl-phenyl) acetamide 31 a (3 g, 0.018 µM) dissolved in toluene (30 ml) in, at room temperature by the addition of phosphorus oxychloride (3.4 g, 0 . 022 µM) stirring at room temperature for 2 hours. Then the cyclohexylamine (2.186 g, 0 . 022 µM) dissolved in toluene (30 ml) is added in the reaction solution in and drop, heating reflux for 12 hours. The reaction fluid evaporation, adding ethyl acetate (50 ml) and saturated sodium bicarbonate solution (50 ml) stirring of the liquid, aqueous phase of ethyl acetate (50 ml x2) extraction, the combined organic phase and saturated salt water (100 ml x 3) washing, the organic phase is dried with anhydrous sodium sulfate, filtered and dryness, preparation HPLC separation and purification to obtain white solid compound 31 b (0.7 g, yield 15.5%), directly used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper(II) acetate monohydrate; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 12 h / 50 °C / Sealed tube 2: copper(II) acetate monohydrate; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With palladium diacetate; copper(II) acetate monohydrate; trifluoroacetic acid In 1,2-dichloro-ethane at 50℃; for 16h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 0 - 25 °C 2: copper(II) acetate monohydrate; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 12 h / 50 °C / Sealed tube 3: copper(II) acetate monohydrate; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 0 - 25 °C 2: copper(II) acetate monohydrate; palladium diacetate; trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With [bis(acetoxy)iodo]benzene; In tetrahydrofuran; at 25℃; for 8h;Sealed tube; Neutral conditions; | General procedure: A vial containing a stirring bar and sealed with a Teflon-linedcap was charged with a mixture of 2-methylacetanilide (1a, 0.2mmol), PhI(OAc)2 (0.4 mmol), and HN(SO2Ph)2 (2a, 0.3mmol).THF (2 mL) was added, and the mixture was stirred at 25 C for8 h. The mixture was then added to H2O (15 mL), and the resultingmixture was extracted with EtOAc (3 × 10 mL). The organiclayers were combined, dried (MgSO4), filtered, and concentratedin vacuo. The residue was purified by column chromatography[silica gel, EtOAc-PE (2:1)] to give a white solid; yield: 64.0 mg(72%); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C | ||
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C 3: dichloromethane / 6 h / 20 °C | ||
Multi-step reaction with 3 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C 3: dichloromethane / 6 h / 20 °C / Darkness |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C 3: dichloromethane / 6 h / 20 °C | ||
Multi-step reaction with 3 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 °C 3: dichloromethane / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C 3: dichloromethane / 6 h / 20 °C | ||
Multi-step reaction with 3 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 °C 3: dichloromethane / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C | ||
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C | ||
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis(trichloromethyl) carbonate 2: tetrahydrofuran / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: 2,6-dimethylnitrobenzene With sodium tetrahydroborate In water at 60 - 70℃; Green chemistry; Stage #2: acetic anhydride In water at 60 - 70℃; Green chemistry; | A typical procedure for reductive-acetylation of nitrobenzene General procedure: In a round-bottom flask (10 mL) equipped with a magnetic stirrer, a mixture of nitrobenzene (0.123 g, 1 mmol) and H2O(2 mL) was prepared. Fe3O4SiO2Cu-Ni-Fe-CrLDH (10 mg) was then added and the mixture was stirred for 5 min. Next, NaBH4 (0.076 g, 2 mmol) was added and the reaction mixture was stirred magnetically for 3 min at 60-70 °C. TLC monitored the progress of the reaction (eluent, n-hexane / EtOAc: 5/2). Ac2O (0.102 g, 1 mmol) was then added and the reductive-acetylation was occurred immediately at 60-70 °C. After formation of acetanilide, the core-shell nanocatalyst was separated by an external magnet and the reaction mixture was extracted with EtOAc(2 × 5 mL). The organic layer was dried over anhydrous Na2SO4 followed by evaporation of the solvent to afford pure acetanilide in 96% yield (Table 4, entry 1). |
92% | Stage #1: 2,6-dimethylnitrobenzene In water for 0.0833333h; Stage #2: With sodium tetrahydroborate In water at 65℃; for 0.0833333h; Stage #3: acetic anhydride In water at 65℃; for 0.0333333h; | |
92% | With sodium tetrahydroborate at 80℃; for 0.183333h; | 2.7. A typical procedure for reductive-acetylation of nitrobenzene toacetanilide with NaBH4/MMTFe3O4Cu MNPs system General procedure: In a round-bottom flask (10 mL) containing H2O (2 mL),nitrobenzene (0.123 g, 1 mmol) and MMTFe3O4Cu MNPs(20 mg) was added and the resulting mixture was stirred vigorouslyin an oil bath (60 °C) for 3 min. Next, NaBH4 (0.114 g,3 mmol) was added to the prepared suspension and the mixturewas stirred under oil bath conditions (60 °C) for additional 5 min.After completion of the reaction (monitored by TLC, eluent: n-hexane:EtOAc = 5:1) and without the isolation of the prepared aniline,Ac2O (0.102, 1 mmol) was added to the reaction mixture. It wascontinued to stir under oil bath conditions (60 °C) for 2 min toafford acetanilide as a sole product. Completion of the reactionwas again monitored by TLC (eluent: n-hexane:EtOAc = 5:1). Afterthat, the magnetic nanocatalyst was separated from the reactionmixture using an external magnetic field. The mixture was thenextracted with EtOAc (2 4 mL) and the combined extracts weredried over anhydrous Na2SO4. Evaporation of the solvent underreduced pressure affords the pure acetanilide in 97% yield(0.111 g, Table 6, entry 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In tetrahydrofuran; toluene for 0.5h; Industrial scale; | 1-5 The method for chemical synthesis of 2,6-dimethylanilinylthiazine according to the invention has the following steps: 1. In a 500 ml clean and dry three-necked flask, add 80 ml of anhydrous tetrahydrofuran, 80 ml of anhydrous toluene, 18 g of acetyl-2,6-dimethylaniline, 5 g of 50% sodium hydride, and add 16 g of carbon disulfide. Stir for 0.5 hours.After pouring 1 time of ice water for 1 hour, the layer was allowed to stand, and the toluene layer was mainly 2,6-dimethylphenyl isothiocyanate; 2. After the organic matter of the toluene layer obtained in the previous step is dried and concentrated by liquid removal, 16 g of 3-aminopropanol is added, and the reaction is stirred at 50 to 80 ° C for 1 to 3 hours. After the reaction is completed, 1-(2,6-dimethylphenyl)-3-(3-propanol)thiourea is obtained; 3. After the above liquid is slightly cooled, 160 ml of concentrated hydrochloric acid is added, heated to 80-95 ° C, and the reaction is stirred for 1 to 3 hours, and the reaction is completed, and cooled to room temperature; 4, standing layering, adding 5 grams of activated carbon to the water layer for decolorization and filtration.The pH was adjusted to 8 to 12 with 20% liquid alkali, and a white solid was precipitated, washed with water, and recrystallized from ethanol to obtain a white crystalline powder of 2,6-dimethylanilinylthiazine 42 g, yield 95%, MP: 136~ 138 ° C (literature value 140 ~ 141 ° C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With tetrakis(triphenylphosphine) palladium(0); 1,4-di(diphenylphosphino)-butane In dichloromethane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid at 80℃; for 3h; | Synthesis of amines 3a-f (general procedure). General procedure: Compound1a,b (0.15 mol), the specifi ed acetanilide (2a-d) (0.21 mol), andTFA (0.9 mol) were charged into a fl at-bottom fl ask equippedwith a refl ux condenser and electromagnetic stirrer (the reactantmolar ratio 1a,b : 2a-d : TFA = 1 : 1.4 : 6). The reaction mixturewas stirred for 3 h at 80 °C. After completion of the reaction, TFAwas distilled off , the residue was hydrolyzed with 10% hydrochloricacid and fi ltered. A 20% sodium hydroxide solution wasadded to the fi ltrate with cooling (up to highly alkaline medium).The precipitate was collected on a fi lter and dried in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid at 80℃; for 3h; | Synthesis of amines 3a-f (general procedure). General procedure: Compound1a,b (0.15 mol), the specifi ed acetanilide (2a-d) (0.21 mol), andTFA (0.9 mol) were charged into a fl at-bottom fl ask equippedwith a refl ux condenser and electromagnetic stirrer (the reactantmolar ratio 1a,b : 2a-d : TFA = 1 : 1.4 : 6). The reaction mixturewas stirred for 3 h at 80 °C. After completion of the reaction, TFAwas distilled off , the residue was hydrolyzed with 10% hydrochloricacid and fi ltered. A 20% sodium hydroxide solution wasadded to the fi ltrate with cooling (up to highly alkaline medium).The precipitate was collected on a fi lter and dried in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With palladium (II) nanoparticles supported on Schiff-base modified clinoptilolite nanocatalyst In neat (no solvent) at 20℃; for 0.333333h; Green chemistry; chemoselective reaction; | 2.4 General procedure for N-acylation of amines General procedure: Pd(at)MCP (0.012g) was added to a mixture of amine (1mmol) and acetic acid (1.2mmol) and the whole mixture was stirred in a round bottomed flask at room temperature for the appropriate time (Table 3). The reaction progress was followed by GC and TLC (eluent, n-hexane:ethyl acetate, 4:1). After completion of the reaction, EtOAc (10mL) was added to the reaction mixture, and the resulting mixture filtered. The filtrate was washed with 1M HCl (3×5mL) and then the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuum to obtain pure N-acylated products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tetrakis(tetrabutylammonium)decatungstate(VI); 2,4,6-Triisopropylthiophenol; water-d2 In acetonitrile for 48h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With C28H26ClN3ORuS In 1,4-dioxane at 100℃; for 8h; Sealed tube; Inert atmosphere; | 2.4 Representative procedure for transamidation reaction General procedure: A mixture of amide (5 mmol), amine (5 mmol) and catalyst (0.5 mol %) in 1,4 dioxane (5 mL) was stirred in a sealed tube under nitrogen atmosphere at 100 C for 8 h. Then the solvent was removed using rotavator and the resulting crude product was purified by column chromatography on silica gel (200-400 mesh) using eluents hexane and ethyl acetate [95:5, v/v] to afford corresponding amides as a white solid. The formation of products was confirmed by NMR spectroscopy. The reported isolated yields are an average of two runs. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0 - 5 °C 1.2: 14 h / 80 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); cesium fluoride; 4-(tert-butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole / tetrahydrofuran / 4 h / 80 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0 - 5 °C 1.2: 14 h / 80 °C 2.1: sodium iodide; hydrogenchloride / acetonitrile; water / 4.5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | Stage #1: N-(2,6-dimethylphenyl)acetamide With 2-bromo-pyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78℃; for 0.666667h; Inert atmosphere; Stage #2: Propyl isocyanate In dichloromethane at -78 - 20℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With Aluminum Chloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; | 13.2 Step 2. Compound 5 Aluminum trichloride (9.6g, 72.0mmol, 3.0eq) was added to dichloromethane (100mL), the reaction mixture was cooled to 0°C under nitrogen protection, and compound 3 (4.0g, 24.0mmol, 1.0eq) was slowly added ) and compound 4 (7.4 g, 36.6 mmol, 1.5 eq) in dichloromethane (50 mL).The reaction was slowly warmed to room temperature, stirred for 16 hours, diluted with dichloromethane (100 mL), and washed with ice water (5 x 200 mL).The separated organic phase was dried over anhydrous sodium sulfate, and concentrated to obtain crude compound 5 (6.0 g).The crude compound 5 was slurried with a mixed solvent of dichloromethane/petroleum ether (20 mL/40 mL) and filtered to obtain compound 5 (4.0 g, yield 58%) as a white solid. |
Tags: 2198-53-0 synthesis path| 2198-53-0 SDS| 2198-53-0 COA| 2198-53-0 purity| 2198-53-0 application| 2198-53-0 NMR| 2198-53-0 COA| 2198-53-0 structure
[ 25027-73-0 ]
N-(4-(Aminomethyl)phenyl)acetamide hydrochloride
Similarity: 0.89
[ 1027-14-1 ]
2-(Diethylamino)-N-mesitylacetamide hydrochloride
Similarity: 0.88
[ 1131-01-7 ]
N-(2,6-Dimethylphenyl)chloroacetamide
Similarity: 0.86
[ 25027-73-0 ]
N-(4-(Aminomethyl)phenyl)acetamide hydrochloride
Similarity: 0.89
[ 1027-14-1 ]
2-(Diethylamino)-N-mesitylacetamide hydrochloride
Similarity: 0.88
[ 25027-73-0 ]
N-(4-(Aminomethyl)phenyl)acetamide hydrochloride
Similarity: 0.89
[ 1027-14-1 ]
2-(Diethylamino)-N-mesitylacetamide hydrochloride
Similarity: 0.88
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P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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