Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 92-50-2 | MDL No. : | MFCD00020575 |
Formula : | C10H15NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HYVGFUIWHXLVNV-UHFFFAOYSA-N |
M.W : | 165.23 | Pubchem ID : | 62338 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.42 |
TPSA : | 23.47 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) : | -5.82 cm/s |
Log Po/w (iLOGP) : | 2.05 |
Log Po/w (XLOGP3) : | 2.1 |
Log Po/w (WLOGP) : | 1.51 |
Log Po/w (MLOGP) : | 1.83 |
Log Po/w (SILICOS-IT) : | 1.46 |
Consensus Log Po/w : | 1.79 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.29 |
Solubility : | 0.841 mg/ml ; 0.00509 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.22 |
Solubility : | 0.988 mg/ml ; 0.00598 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.75 |
Solubility : | 0.293 mg/ml ; 0.00177 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
99.4% | at 102 - 133℃; for 4 h; Autoclave; Inert atmosphere; Industrial scale | The autoclave was purged with nitrogen and under nitrogen protection, 24.2 kg (200 mol) of N-ethylaniline, 8.9 kg (202 mol) of ethylene oxide, 242 g (1.9 mol) of taurine were added, and the autoclave was closed. Cap, and tighten, open the heating, heating to 102 °C at a heating rate of 1 °C / min, stop heating, the reaction temperature rose to 133 °C reaction 4. Oh, after the reaction is completed, cooled to 40 °C, discharge, 32.8 kg of N-ethyl-N-hydroxyethylaniline was obtained in a yield of 99.4percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.4% | With Tau; at 102 - 133℃; for 4h;Autoclave; Inert atmosphere; Industrial scale; | The autoclave was purged with nitrogen and under nitrogen protection, 24.2 kg (200 mol) of N-ethylaniline, 8.9 kg (202 mol) of ethylene oxide, 242 g (1.9 mol) of taurine were added, and the autoclave was closed. Cap, and tighten, open the heating, heating to 102 C at a heating rate of 1 C / min, stop heating, the reaction temperature rose to 133 C reaction 4. Oh, after the reaction is completed, cooled to 40 C, discharge, 32.8 kg of N-ethyl-N-hydroxyethylaniline was obtained in a yield of 99.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With trichlorophosphate; In tetrahydrofuran; at 20℃; for 5h; | The procedure described in Ref. [49] was used to prepare N-ethyl-N-(2-chloroethyl) aniline. A solution of POCl3 (3.30 g, 0.021 mol) in 10 mL of THF was added dropwise to a solution of N-ethyl-N-(2-hydroxyethyl)aniline(5.00 g, 0.03 mol) in THF under intensive stirring at room temperature for one hour. The reaction mixture was stirred for 4 h. The solvent was evaporated, the residue was diluted with an aqueous solution of NaHCO3, the product was extracted with CH2Cl2 (20 mL). The extract was dried over MgSO4, filtered, and the solvent was distilled off in a vacuum of a water jet pump. The product was purified by vacuum distillation, selecting the fraction with Tb = 65-73 C/0.4mm Hg. Yield: 3.5 g (60%), a liquid of a yellow color was obtained. 1H NMR (400 MHz, acetone d6; delta, ppm; J, Hz): 1.14 (t, 3H, -CH3, J = 7.1), 3.45 (q, 2H, N-CH2-CH3, J = 7.1), 3.66 (s, 4H, -N-CH2CH2-Cl), 6.63 (t, 1, p-Ar-H(-N), J = 8.9), 6.72 (d, 2, o-Ar-H(-N), J = 8.9), 7.17 (t, 2, m-Ar-H(-N), J = 8.9). |
50% | With thionyl chloride; In dichloromethane; for 1h;Reflux; | Compound 3a was published previously.4 In brief, 2-(N-ethyl-N-phenylamino)ethanol (10g, 60mmol) in CH2Cl2 (150mL)was reacted with SOCl2 (8.8mL, 121mmol). The mixture was heated to reflux for one hour and quenched. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide product (5.54g, 30mmol, 50%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) delta 7.28 (m, 2H), 6.74 (m, 3H), 3.65 (m, 4H), 3.46 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C10H15ClN [M+H]+: 184.0893, found: 184.0836. |
50% | With thionyl chloride; In dichloromethane; for 1h;Reflux; | 2-(N-ethyl-N-phenylamino)ethanol (10 g, 60 mmol) in CH2Cl2 (150 mL) was reacted with SOCl2 (8.8 mL, 121 mmol). The mixture was heated to reflux for one hour and quenched. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide intermediate 3a (5.54 g, 30 mmol, 50%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) delta 7.28 (m, 2H), 6.74 (m, 3H), 3.65 (m, 4H), 3.46 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C10H15ClN [M+H]+: 184.0893, found: 184.0836. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In ethanol; at 35 - 40℃; for 2h; | This Example regards the synthesis of 2-(ethyl{4-[(3-methyl-1,3-thiazol-3-ium-2-yl)diazenyl]phenyl}amino)ethyl sulfate (substantive dye 1), and includes the synthesis of 2-[ethyl(phenyl)amino]ethyl hydrogensulfate. 16.5 g (0.10 mol) of <strong>[92-50-2]2-(N-ethylanilino)ethanol</strong> were added at a temperature of 35-40 C. to 25.0 ml of concentrated sulfuric acid. The reaction proceeded slightly exothermically and was kept within the stated temperature range by cooling with ice water. The mixture was stirred for a further two hours. Once the reaction was complete, the mixture was poured onto ice and made up to 250 ml by adding water. A transparent yellow solution was obtained which was used without further work-up in the azo coupling described below. | |
With sulfuric acid; In water; at 35 - 40℃; for 2h; | 1.1. Synthesis of 2-[ethyl(phenyl)amino]ethyl hydrogen sulfate In 1.1, 16.5 grams (g) (0.10 mol) of <strong>[92-50-2]2-(N-ethylanilino)ethanol</strong> were added to 25.0 milliliters (ml) of concentrated sulfuric acid at a temperature of 35 to 40 degrees Celsius ( C.). The reaction proceeded slightly exothermically and was held within the specified temperature range by cooling with iced water. The mixture was stirred for an additional 2 hours. On completion of the reaction, the mixture was poured onto ice and made up to 250 ml by adding water. The result was a transparent yellow solution, which was used in the next stage with no further processing. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium phosphate; 4-methoxy-phenol; at 70℃; under 225.023 Torr; | During this apparatus, hydroquinone monomethyl ether 0.19 g (350 ppm), methyl methacrylate (MMA) 600g (6.0 mol) and N- ethyl--N- hydroxyethyl aniline 165.3g (1.0 mol) and phosphorus anhydride acid potassium 4.25g was charged with (the N- ethyl -N- hydroxyethyl aniline 2.0 mol% as a reference), and the mixture was stirred. Adjusted to vacuum (300mbar), the suspension was heated slowly to 70 C to. Continuously distillate during the reaction (MMA / methanol) was removed and returned Correspondingly reflux ratio. The temperature during the bottoms is 70~75 C, the temperature at the top of the tower was 38-66 C. The reaction was monitored using GC analysis. After 300 minutes, to lower the bath temperature to 60 C, to distill off the unreacted MMA. Completion of the reaction, to stop the vacuum. The suspension was cooled, with continued pressure Buchner funnel, the remaining catalyst was filtered off.A clear solution was obtained in 90% yield ethyl aniline methacrylate having a purity of> 98%. |
With 4-methoxy-phenol;potassium dihydrogenphosphate; at 70℃; under 225.023 Torr; for 5h; | The transesterification was effected in a 750 ml miniplant reactor with Oldershaw column with liquid distributor, internal thermometer, gas inlet and anchor stirrer. The return ratio was 25:1 (return stream:output stream), the stirrer speed of the anchor stirrer was 300 rpm and the air introduction rate was 1.5 l/h.This apparatus was initially charged with 0.19 g (350 ppm) of hydroquinone monomethyl ether, 600 g (6.0 mol) of methyl methacrylate (MMA) and 165.3 g (1.0 mol) of N-ethyl-N-hydroxyethylaniline, and also 4.25 g (2.0 mol %, based on N-ethyl-N-hydroxyethylaniline) of anhydrous potassium phosphate, which were stirred. The vacuum was established (300 mbar) and the suspension was heated gradually to 70 C. During the reaction, distillate (MMA/methanol) was removed continuously and recycled according to the return ratio. The temperature in the bottom was between 70 and 75 C.; the temperature at the top of the column was between 38 and 66 C. The reaction was monitored by means of GC analysis. After 300 min, the bath temperature was reduced to 60 C. and unconverted MMA was distilled off. The reaction was ended and the vacuum was broken. The suspension was cooled and then the remaining catalyst was filtered off using a pressure suction filter.A clear solution was obtained in a yield of 90% of ethylanilineethyl methacrylate with a purity of >98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In tetrahydrofuran; at 0 - 20℃; | Example 4: Other blue colored particles according to the invention; According the general concept, first a neutral precursor particle 110c is produced via the latex 110b. <n="70"/>A mixture of 12.8 g of freshly distilledstyren, 1.6 g of para-divinyl benzene and 1.6 of the precursor monomer 110 a (see below) is emulgated in 183 ml of water containing 0.75 g of sodium dodecyl sulfate for about 45 min at room temperature. After that time 0.05 g of potassium peroxo disulfate are added and the mixture heated to 70 C for 20 h. Purification is performed by repeated precipitation as described in example 1. The latex 110 b is finally taken up in ethanol for the subsequent reaction. To 60 ml of this erthanol suspension (containing 62 mg solid per ml, according 0.51 mmol aniline derivative 110 a based on elemental analysis) and 13 mg of amido sulfonic acid, which is cooled to O0 C are added portionwisse a solution of the known diazonium salt (DE 444 46 382), prepared in situ from 247 mg of 2-amino-7-methoxy benzthiazole, 106 mg sodium nitrite and 0.285 ml 96 % sulfuric acid in 3 ml of water at O0 C, and stirred at 0 C for 3 h. Purification of this material is performed as in axample 1 by repeated centrifugation from ertrhanol and methanol until no starting material can be detected in the supernatants. A final elemental analysis confirms a dye contents of about 0.093 mmol per gram particles 110. The comonomer 110 is prepared from 20.0 g of commercial N-erthyl, N-2-hydroxy ethylene aniline and 18.5 g para-vinyl benzylcholride in 150 ml tetrahydrofuran in the presence of 7.0 g (50 % w/w) sodium hydride at Oo C. The mixture is stirred at room temperature until complete consumption of the starting materials, filtered, evaporated and then purified over a silica gel column (eluent hexane - ethyl acetate : 14 - 1 (v/v)) to give 11.7 g of compound 110.110: 1H-NMR (CDCI3, 300 MHz): delta 1.14 (t, 3 H); 3.39 (q, 2 H); 3.52 (t, 2 H); 3.63 (t, 3 H); 4.50 (s, 3 H); 5.24 (dd, 1 H); 5.76 (dd, 1 H); 6.10 - 6.75 (m, 4 H); 7.16 - 7.28 (m, 2 H); 7.25 (d, 2 H), 7.37 (d, 2 H) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: conc. hydrochloric acid; sodium nitrite / acetone; H2O / 1 h / 0 °C 1.2: 80 percent / acetone; H2O / 2 h / 0 °C 2.1: 49 percent / triethylamine / tetrahydrofuran / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium nitrate; sodium acetate; In hydrogenchloride; water; | (A) Synthesis of naphthalic anhydride dye STR48 Sodium nitrate (1.6 grams, 0.023 mol) was added to 20 mL cold (<10 C.) concentrated H2 SO4. 4-Amino-1,8-naphthalic anhydride (5 grams, 0.023 mol) was added slowly with stirring, keeping the temperature less than 10 C. The diazotization was continued for two hours. N-Ethyl-N-phenylethanolamine (3.8 grams, 0.023 mol) was dissolved in 20 mL concentrated HCl and cooled to less than 10 C. The diazo solution was slowly added to the HCl solution with stirring, keeping the temperature less than 10 C. The solution was stirred for two hours, then poured into a solution containing 50 grams sodium acetate in 600 mL water. A purple solid (3 grams) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; toluene; | Preparation 7 N-ethyl-N-2-methacryloyloxyethylaniline To a stirred solution of N-ethyl-N-2-hydroxyethyl-aniline (4.95g: 0.03 mol) in toluene (50ml) under air was added methylmethacrylate (19ml; 0.178 mol) dioctyltinoxide (1.15g) and 1% topanol 'O' (0.2 ml solution in CH2Cl2). The mixture was heated at reflux under a steady air flow for twelve hours then the contents cooled and evaporated under reduced pressure to give the crude product (8.97g >100%). This was purified by flash chromatography (silica/hexane/ethyl acetate gradient) to give the product as a colourless oil (6.89g; 98%). 1Hnmr (250MHz; CDCl3; TMS 1.3t (3H), 2.0s (3H), 3.5m (4.4t (2H), 5.6s (1H), 6.2s (1H), 6.7m (3H), 7.2m (2H) ir (liquid film) 2950, 1720, 1600, 1500, 1360, 1300, 1160 cmmin1 Analysis found C, 72.4; H, 8.3; N, 5.8 C14H19NO2 requires C, 72.1; H, 8.2; N, 6.0% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide;tetra(n-butyl)ammonium hydrogensulfate; In water; benzene; at 20℃; for 3h; | (b) Synthesis of Aniline Derivative N-(ethyl)-anilino ethanol (1 mmol) is mixed with tertiary butyl bromoacetate (1.1 mmol) in benzene. A 50% NaOH solution is added to the reaction along with tetrabutyl ammonium hydrogen sulfate (phase transfer agent). Stirring continues at room temperature for 3 hours. The organic layer is evaporated to dryness and the product is purified using silica gel chromatography using hexane:ethyl acetate (19:1). | |
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In water; benzene; at 20℃; for 3h; | N-(ethyl)-anilino ethanol (1 mmol) is mixed with tertiary butyl bromoacetate (1 .1 mmol) in benzene. A 50% NaOH solution is added to the reaction along with tetrabutyl ammonium hydrogen sulfate (phase transfer agent). Stirring continues at room temperature for 3 hours. The organic layer is evaporated to dryness and the product is purified using silica gel chromatography using hexane:ethyl acetate (19:1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With NaH; In tetrahydrofuran; | REFERENCE EXAMPLE 1 Preparation of 4-([N-Ethyl-N-phenyl-2-aminoethyl]oxymethyl)phenyl phenyl diazomethane (XVI) 4-([N-Ethyl-N-phenyl-2-aminoethyl]oxymethyl) benzophenone (XIV) 2-(N-Ethylanilino)ethanol (3.03 g, 18.4 mmol, 1.2 eq) in THF (20 cm3) was treated with NaH (60% dispersion in oil, 524 mg, 13,1 mmol, 1.4 eq) and stirred at 20 C. for 1 hour. 4-Bromomethylbenzophenone (IX) (4.21 g, 15.3 mmol) was then added and stirring continued for 72 hours. Excess solvent was removed in vacuo and the residue diluted with DCM, washed with water and NaHCO3 solution (sat.), dried (MgSO4) and solvent removed under vacuum. The resulting oil was purified by flash chromatography, eluding with petroleum (bp 40-60 C.):EtOAc (9:1), to give the desired product (XIV) as a yellow oil (4.36 g, 80%), Rf=0.54 (4:1, petrol:EtOAc) (Found: C, 78.34; H, 6.86; N, 5.29. C24H25NO2 requires C, 80.19; H, 7.01; N, 3.90%); umax (film/cm-1 1658 (s), 1598 (s), 1506 (s); deltaH (200 MHz; CDCl3) 1.22 (3 H, t, J7, CH3), 3.49 (2 H, q, J7, CH2CH3), 3.58-3.79 (4 H, m, OCH2CH2N), 4.66 (2 H, s, ArCH2O), 6.69-6.79 (3 H, m, ArH o- and p- to NR2), 7.28 (2 H, dd, J7, 7, ArH m- to NR2), 7.46-7.68 (5 H, m, ArH), 7.80-7.88 (4 H, m, ArH o- to C=O); deltaC (50.3 MHz; CDCl3) 12.2 (CH3), 45.5 (NH2CH3), 50.1 (NCH2CH2O), 68.5 (NCH2CH2O), 72.2 (ArCH2O), 111.8 (ArCH o- to NR2), 115.8 (ArCH p- to NR2), 127.0, 128.3, 129.3, 130.0 and 130.3 (ArCH o- and m- to C=O and ArCH m- to NR2), 132.4 (ArCH p- to C=O), 136.8 and 137.7 (40 ArCC=O), 143.2 (40 ArCCH2O), 147.7 (40 ArCNR2),196.4 (C=O); n/z (APCI+) 360 ([M +H]+, 30%); HRMS C24H26O2N requires 360.1963; found 360.1963. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | 1.3 g (18.56 mmol) sodium nitrite was added in small portions to 13.2 g conc. sulphuric acid and cooled to 0 C and diluted with 4.8 ml propionic acid and 19.2 ml acetic acid. 3.0 g (18.45 mmol) <strong>[76874-79-8]2-amino-4-chloro-1,3-thiazole-5-carbaldehyde</strong> were then added in small portions. The viscous reaction mixture was stirred for 2 hours at 0 C. This mixture was then added slowly to a solution of 3.2 g (18.56 mmol) 2-[ethyl(phenyl)amino]ethanol in 180 ml water, containing 6 ml sulphuric acid. After stirring for another 2 hours at room temperature, the obtained precipitate was filtered off, washed with water and dried at 40 C in vacuum. Yield: 3.58 g (57%) 1H NMR (d6-DMSO/300 MHz): delta = 1.20 (t, J= 6.9 Hz, 3H, CH3), 3.47-3.55 (m, 6H, 3xCH2), 3.96 (s, br., 1H, OH), 7.03 (d, J= 9.0Hz, 2H, phenyl), 7.84 (d, J= 9.0 Hz, 2H, phenyl), 9.92 (s, 1H, formyl). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In dichloromethane; at 0℃; for 1h; | N-Ethyl-(2-anilino) ethanol (91.5 g, 554 mmol) was dissolved in 1400 mL of CH2Cl2 and Et3N (192.4 mL, 1385 mmol) was <n="20"/>added. The solution was cooloed to 00C and Methanesulfanonyl chloride (51.8mL, 665 mmol) was slowly added over 30 min. After 0.5 h, the reaction was diluted with 500 mL CH2Cl2 and washed successively with 500 mL of 2 % HCl (x2), then 500 mL water, and 500 mL of saturated NaCl. The organic phase was passed over a pad of Na2SO4, and evaporated to light brown-colored oil (135 g, 554 mmol, 100 %). 1H NMR (CDCl3, 300 mHz) delta 7.25-7.19 (m, 2 H), 6.73-6.68 (m, 3 H), 4.33 (t, J= 6.2 Hz, 2 H), 3.65 (t, J= 6.2 Hz, 1 H), 3.41 (q, J= 7.1 Hz, 2 H), 2.96 (s, 3 H), 1.16 (t, J= 7.1 Hz, 3 H). Sodium Azide (17.4 g, 267 mmol) was added to the above material and diluted with 600 mL of DMSO. The flask was heated to 70 0C and stirred for 1.5 h and cooled to room temperature. The solution was diluted with 1500 mL of water and extracted with 600 mL of Et2O three times. The combined organic phase was washed three times with 800 mL of water and then once with 800 mL of saturated NaCl. The organic phase was passed over Na2SO4 and evaporated to leave 2 as a thick oil (101 g, 531 mmol, 96%.) 1H NMR (CDCl3, 300 mHz) delta 7.31-7.22 (m, 2 H), 6.77-6.69 (m, 3 H), 3.56-3.42 (m, 6 H), 1.19 (t, J= 10.6 Hz, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 18h; | <strong>[92-50-2]2-(N-ethylanilino)ethanol</strong> (1 equiv.), NaH (2 equiv.), and tosyl chloride (1.2 equiv.) were dissolved in DMF and stirred at room temperature for 18 h. The solution was processed through an aqueous workup. The organics were dried over MgSO4 and the solvents were removed en vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77.0% | Disperse Orange 3 (0.97 g, 0.004 mol) was dissolved in 60 ml of 0.3M aqueous hydrochloric acid solution at room temperature. The solution was cooled to 0-5 C, and 0.004 mol of sodium nitrite was added and stirred for 1 h. Then, a small portion of sulfamic acid was added as a nitrous acid scavenger. The resulting diazonium salt solution was added to a coupling component solution of <strong>[92-50-2]2-(N-ethylanilino)ethanol</strong> (0.66 g, 0.004 mol) dissolved in 20 ml of ethanol and 30 ml of water, while maintaining the temperature and pH of the mixture at 0-5 C and 5-6, respectively, during the course of addition. The reaction mixture was stirred for 2 h, and the precipitate was filtered, washed with brine and ethanol, and dried in a vacuum oven. The crude product (US2) was purified by recrystallization in methylene chloride. US2: Yield 77.0%; 1H NMR (DMSO-d6, ppm): 1.16 (t, 3H, CH3), 3.53 (m, 4H, CH2), 3.62 (m, 2H, CH2), 4.84 (t, 1H, OH), 6.86 (d, 2H, ArH), 7.82 (d, 2H, ArH), 7.97 (d, 2H, ArH), 8.11 (d, 4H, ArH), 8.44 (d, 2H, ArH); Mass: m/z 418.18 (100%, [M + H]); Found: C, 63.05; H,5.36; N, 20.42. Calc. for C22H22N6O3: C, 63.15; H, 5.30; N, 20.08. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Example 4; Preparation of Methacrylate Ester Derivative of Cl Basic Blue 41; Stage 1; 2-Amino-6-methoxybenzothiazole (18.0 g) is stirred in a mixture of acetic acid (70 ml) and propionic acid (50 ml) at 50 C. The resulting solution is cooled to -10 C. Nitrosylsulphuric acid solution (40 weight-% in sulphuric acid) (32.0 g) is added dropwise. This mixture is added to a stirred solution of N-ethyl-N-(2-hydroxyethyl) aniline and sulphamic acid (1.0 g) in acetic acid (25 ml) and ice/water (100 ml). After 20 minutes, the pH is raised to 4 by the dropwise addition of potassium hydroxide solution. A tarry residue is formed; the mixture is stirred for a further 2 hours until the tar solidifies. This solid is collected, washed with water and then dissolved in alcohol and acetone to give a deep red solution. Hot water is added to precipitate a solid which is removed by filtration. The solid is washed with cold alcohol and dried (29.5 g, 83% yield) Mp 178-179 C. | |
83% | 2-Amino-6-methoxybenzothiazole (18.0 g) 1sstirred in a mixture of acetic acid (70 ml) and propionic acid(50 ml) at 50 C. The resulting solution is cooled to -10 C.Nitrosylsulphuric acid solution (40 weight-% in sulphuricacid) (32.0 g) is added dropwise. This mixture is added to astirred solution of N-ethyl-N-(2-hydroxyethyl) aniline andsulphamic acid (1.0 g) in acetic acid (25 ml) and ice/water(100 ml). After 20 minutes, the pH is raised to 4 by thedropwise addition of potassium hydroxide solution. A tarryresidue is formed; the mixture is stirred for a further 2 hoursuntil the tar solidifies. This solid is collected, washed withwater and then dissolved in alcohol and acetone to give adeep red solution. Hot water is added to precipitate a solidwhich is removed by filtration. The solid is washed with coldalcohol and dried (29.5 g, 83% yield) Mp 178-179 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | 52.06 g (0.25 mol) of phosphorus pentachloride was slowly added to 150 mL of DMF cooled in an ice bath and the ice bath was continued for 30 minutes and then stirred at room temperature for 15 minutes. To the above system, 20 g (0.12 mol) of N-ethyl-N-hydroxyethylaniline was slowly added. After stirring at a temperature of 45 C for 12 hours, the mixture was returned to room temperature and the reaction solution was neutralized with sodium bicarbonate solution. The reaction solution was extracted three times with methylene chloride. The dichloromethane extract was washed with water to neutral and then dried over anhydrous magnesium sulfate. After filtration, the dichloromethane was removed by steaming,24.9 g of the corresponding intermediate product Q2-1 was obtained (yield 98%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: A solution of sodium nitrite (5.5 mmol) in 2.2 ml water was added dropwise with stirring to a cooled solution of 4,4?-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline (DA-I) (1.0 g, 2.7 mmol) dissolved in 3.0 ml concentrated hydrochloric acid 18% (16.5 mmol) at a temperature between 0 and 5 C for 2 h. The resulting diazonium salt was coupled with 2-[ethyl(phenyl)amino] ethanol (0.91 g, 5.5 mmol) dissolved in 5.8 ml hydrochloric acid 1.8% at a temperature between 0 and 5 C over 2 h. Then sodium acetate was added, the solution was left in an ice bath for 1 h, additional sodium acetate was added, and the reaction mixture was left for 30 min. After the temperature increased to room temperature, sodium hydroxide solution was added until the pH of the solution reached 6 and the mixture was stirred at room temperature for 1 h. The obtained monomer was washed with water and recrystallized from ethanol. This general procedure was used for all the obtained diamines. Yield: 0.71 g (65%). Melting point (m.p): 180-183 C. 1H NMR (DMSO-d6): 7.82 ppm (d, 4, J = 8.82 Hz, Ar-H), 7.78 ppm (d, 4, J = 8.82 Hz, Ar-H), 7.4 ppm (d, 4, J = 8.82 Hz, Ar-H), 6.84 ppm (d, 4, J = 8.82 Hz, Ar-H), 4.83 ppm (t, 2, J = 4.67, OH), 3.61 ppm (q, 4, J = 4.67, CH2), 3.5 ppm (m, 8, CH2), 1.15 ppm (t, 6, J = 6.75 Hz, CH3). 19F NMR: -156.65 ppm (s, 4F, Ar-F). IR (KBr): 3371 cm-1 (OH), 3072 cm-1 (-), 2966 cm-1 (CH3), 2926 cm-1 (CH2), 2872 cm-1 (CH3), 1392 cm-1 (), 1601, 1512, 1489 cm-1 (Ar), 1005, 991 cm-1 (-F). UV-vis: lambdamax = 432 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: A solution of sodium nitrite (5.5 mmol) in 2.2 ml water was added dropwise with stirring to a cooled solution of 4,4?-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline (DA-I) (1.0 g, 2.7 mmol) dissolved in 3.0 ml concentrated hydrochloric acid 18% (16.5 mmol) at a temperature between 0 and 5 C for 2 h. The resulting diazonium salt was coupled with 2-[ethyl(phenyl)amino] ethanol (0.91 g, 5.5 mmol) dissolved in 5.8 ml hydrochloric acid 1.8% at a temperature between 0 and 5 C over 2 h. Then sodium acetate was added, the solution was left in an ice bath for 1 h, additional sodium acetate was added, and the reaction mixture was left for 30 min. After the temperature increased to room temperature, sodium hydroxide solution was added until the pH of the solution reached 6 and the mixture was stirred at room temperature for 1 h. The obtained monomer was washed with water and recrystallized from ethanol. This general procedure was used for all the obtained diamines. Yield: 0.71 g (65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: A solution of sodium nitrite (5.5 mmol) in 2.2 ml water was added dropwise with stirring to a cooled solution of 4,4?-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline (DA-I) (1.0 g, 2.7 mmol) dissolved in 3.0 ml concentrated hydrochloric acid 18% (16.5 mmol) at a temperature between 0 and 5 C for 2 h. The resulting diazonium salt was coupled with 2-[ethyl(phenyl)amino] ethanol (0.91 g, 5.5 mmol) dissolved in 5.8 ml hydrochloric acid 1.8% at a temperature between 0 and 5 C over 2 h. Then sodium acetate was added, the solution was left in an ice bath for 1 h, additional sodium acetate was added, and the reaction mixture was left for 30 min. After the temperature increased to room temperature, sodium hydroxide solution was added until the pH of the solution reached 6 and the mixture was stirred at room temperature for 1 h. The obtained monomer was washed with water and recrystallized from ethanol. This general procedure was used for all the obtained diamines. Yield: 0.71 g (65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | General procedure: A solution of sodium nitrite (5.5 mmol) in 2.2 ml water was added dropwise with stirring to a cooled solution of 4,4?-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline (DA-I) (1.0 g, 2.7 mmol) dissolved in 3.0 ml concentrated hydrochloric acid 18% (16.5 mmol) at a temperature between 0 and 5 C for 2 h. The resulting diazonium salt was coupled with 2-[ethyl(phenyl)amino] ethanol (0.91 g, 5.5 mmol) dissolved in 5.8 ml hydrochloric acid 1.8% at a temperature between 0 and 5 C over 2 h. Then sodium acetate was added, the solution was left in an ice bath for 1 h, additional sodium acetate was added, and the reaction mixture was left for 30 min. After the temperature increased to room temperature, sodium hydroxide solution was added until the pH of the solution reached 6 and the mixture was stirred at room temperature for 1 h. The obtained monomer was washed with water and recrystallized from ethanol. This general procedure was used for all the obtained diamines. Yield: 0.71 g (65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | General procedure: A solution of sodium nitrite (5.5 mmol) in 2.2 ml water was added dropwise with stirring to a cooled solution of 4,4?-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline (DA-I) (1.0 g, 2.7 mmol) dissolved in 3.0 ml concentrated hydrochloric acid 18% (16.5 mmol) at a temperature between 0 and 5 C for 2 h. The resulting diazonium salt was coupled with 2-[ethyl(phenyl)amino] ethanol (0.91 g, 5.5 mmol) dissolved in 5.8 ml hydrochloric acid 1.8% at a temperature between 0 and 5 C over 2 h. Then sodium acetate was added, the solution was left in an ice bath for 1 h, additional sodium acetate was added, and the reaction mixture was left for 30 min. After the temperature increased to room temperature, sodium hydroxide solution was added until the pH of the solution reached 6 and the mixture was stirred at room temperature for 1 h. The obtained monomer was washed with water and recrystallized from ethanol. This general procedure was used for all the obtained diamines. Yield: 0.71 g (65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: A solution of sodium nitrite (5.5 mmol) in 2.2 ml water was added dropwise with stirring to a cooled solution of 4,4?-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline (DA-I) (1.0 g, 2.7 mmol) dissolved in 3.0 ml concentrated hydrochloric acid 18% (16.5 mmol) at a temperature between 0 and 5 C for 2 h. The resulting diazonium salt was coupled with 2-[ethyl(phenyl)amino] ethanol (0.91 g, 5.5 mmol) dissolved in 5.8 ml hydrochloric acid 1.8% at a temperature between 0 and 5 C over 2 h. Then sodium acetate was added, the solution was left in an ice bath for 1 h, additional sodium acetate was added, and the reaction mixture was left for 30 min. After the temperature increased to room temperature, sodium hydroxide solution was added until the pH of the solution reached 6 and the mixture was stirred at room temperature for 1 h. The obtained monomer was washed with water and recrystallized from ethanol. This general procedure was used for all the obtained diamines. Yield: 0.71 g (65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.5% | (£)-2-{Ethyl-{4-[(4-fluorophenyl)diazenyl]phenyl}amino}ethanol 13. 13 An ice-cooled solution of sodium nitrite (3.45 g, 50.0 mmol, 30% aq. w/w) was added to a solution of 4-fluoroaniline (5.55 g, 50.0 mmol) dissolved in 6 M hydrochloric acid (30 mL) at 0 C. The mixture was stirred for 0.5 h and a solution of 2-[ethyl(phenyl)amino]ethanol (8.26 g, 50.0 mmol) dissolved in 6 M hydrochloric acid (30 mL) was added dropwise. The resulting deep coloured slurry was warmed to 20 C over 1 h: then, it was treated with 3 M sodium acetate (50 mL). The fine slurry was filtered under suction and the press cake was washed thoroughly with water and dried in air. Compound 13 (13 g, 90.5%) was obtained as bright orange solid, mp 106-107 C; <5H (200 MHz, CDCI3): 7.90-7.79 (4H, m), 7.22-7.10 (2H, m), 6.85-6.75 (2H, m), 3.87 (2H, t, J 5.8 Hz), 3.64-3.46 (4H, m), 1 .24 (3H, t, J 7.0 Hz); ESI (m/z, +c): 288.2 (100%) [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-Amino-5-nitro-[2,1]-benzisothiazole (1.95g, 10.0mmol) was dissolved in a mixture of concentrated sulfuric acid (2mL) and glacial acetic acid (10mL) at -5C in an ice-salt bath. Sodium nitrite (0.76g, 11.0mmol) was dissolved in cold water and added dropwise to the reaction mixture for 0.5h under stirring. The diazonium salt was obtained and used for the next coupling reaction. N-Ethyl-N?-phenylethanolamine (2.07g, 10.0mmol) was added to a mixture of methanol/water (90mL, 2:1, v/v) solution in a three-necked flask immersed in an ice bath. Freshly prepared diazonium salt was added dropwise for 1h to the reaction mixture under vigorous mechanical stirring (0-5C). After additional stirring for 1.5h, the mixture was neutralized with aqueous ammonia to pH 5-6, and the precipitate was filtered and dried after thorough washing with ethanol and water. The crude product was recrystallized by acetonitrile and water (v/v=5:1), and the microcrystals of dye 1 were finally obtained. Yield, 2.12g (57%). M.p. 206-208C; Main FT-IR absorptions (KBr pellets, nu, cm-1): 3344 (w), 1736 (s), 1660 (s), 1597 (vs), 1519 (s), 1410 (vs), 1255 (vs), and 1122 (vs). 1H NMR (500MHz, CDCl3, ppm): delta 9.23 (s, 1H, benzisothiazole), 8.23 (dd, 1H, J=2.2 and 9.6Hz, benzisothiazole), 8.00 (d, 2H, J=9.2Hz, phenyl), 7.79 (d, 1H, J=9.6Hz, benzisothiazole), 6.88 (d, 2H, J=9.2Hz, phenyl), 3.97 (t, 2H, CH2OH), 3.71 (t, 2H, NCH2), 3.66 (q, 2H, NCH2), 1.33 (t, 3H, CH3). Blue single crystals of dye 1 suitable for X-ray diffraction measurement were obtained from a mixture of acetonitrile and ethanol (v:v=1:1) by slow evaporation in air at room temperature for one week. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.1% | General procedure: o-Tolidine (0.85 g, 0.004 mol) was dissolved in 40 ml of 1 M aqueous hydrochloric acid solution at room temperature. The solution was cooled to 0-5 C and 0.008 mol of sodium nitrite was added and stirred for 1 h. Then, a small portion of sulfamic acid was added as a nitrous acid scavenger. The resulting diazonium salt solution was added to a coupling component solution of 2-diethylamino-phenol (1.32 g, 0.008 mol) dissolved in 50 ml of water, while maintaining the temperature and pH of the mixture at 0-5 C and 5-6, respectively, during the course of addition. The reaction mixturewas stirred for 2 h and the precipitate was filtered. The crude product (BP1) was washed with brine and ethanol and dried in a vacuum oven. The other BP series dyes were prepared in a similar manner. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.3% | General procedure: 4,4'-Diaminostilbene-dihydrochloride (0.56 g, 0.002 mol) was dissolved in 30 ml of 0.6 M aqueous hydrochloric acid solution at room temperature. The solution was cooled to 0-5 C and 0.004 mol of sodium nitrite was added and stirred for 1 h. Then, a small portion of sulfamic acid was added as a nitrous acid scavenger. The resulting diazonium salt solution was added to a coupling component solution of 2-(N-ethylanilino)-ethanol (0.66 g,0.004 mol) dissolved in 20 ml of ethanol and 30 ml of water, while maintaining the temperature and pH of the mixture at 0-5 C and 4-5, respectively, during the course of addition. The reaction mixture was stirred for 2 h and the precipitate was filtered. The crude product (ST3) was washed with brine and ethanol and dried in a vacuum oven. The other ST series dyes were prepared in a similar manner. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine; at 55℃; for 2h; | N-Ethyl-N-(2-methacryloyloxyethyl)aniline Methacryloyl anhydride (18.5 g, 0.12 mol) is added dropwise to a stirred solution of N-ethyl-N-(2-hydroxyethyl)-aniline (16.5 g, 0.1 mol) in pyridine. The mixture is stirred at 55 C. for 2 hours, poured onto ice/water and extracted with hexane. The organic layer is passed through silica gel eluted with hexane, followed by removal of solvent to yield N-ethyl-N-(2-methacryloyloxyethyl)aniline (17.4 g, 70%), as a pale yellow oil. |
0.282 mol | With triethylamine; In dichloromethane; at 40℃; | 0.300 mol of N-ethyl, N-hydroxyethylaniline and 0.330 mol of triethylamine were dissolved in 200 mL of dichloromethane and dissolved by stirring. Then, 0.330 mol of methacrylic anhydride was added, and the temperature was raised to 40 C and maintained. After completion of the reaction, water was added and the layers were separated, and 50 mL of a saturated sodium chloride solution was further added, followed by stirring for 30 minutes. After the layer separation, the organic layer was dried under reduced pressure and purified to obtain 0.282 mol of the formula IV. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrogenchloride; ammonia; sodium nitrite; In water; at 5℃;pH 1.5 - 2; | Stage 1. 2-[Ethyl(4-nitrosophenyl)amino]ethanol 2N Sodium nitrite is added dropwise to a stirred solution of N-ethyl-N-beta-hydroxyethyl (16.5 g, 0.1 mol) in dilute hydrochloric acid, keeping the temperature below 5 C. and the pH at 1.5 to 2.0, until all of the starting material is consumed. Ammonia solution is added until the pH 9 is reached and the resulting oil is extracted with methylene chloride. Removal of solvent affords a greenish oil. Yield 16 g, 82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | The synthesis was as shown in Scheme 1 below. Cold concentrated HCl (4.25 mL) was added to a suspension of 4-nitro-1-naphthylamine (0.5 g, 2.66 mmol) in water (1.6 mL) at 0 C. A solution of NaNO2 (0.4 g) in water (1 mL) was added dropwise at 0 C. over 15 min and the 4-nitro-1-naphthylamine dissolved upon stirring. The solution was allowed to react for 10 min and then urea (0.16 g) was slowly added. Next, a solution of N-ethyl-N-hydroxyethylaniline (0.45 g) in acetic acid (2.18 mL) was mixed into the solution. After 15 mins, sodium acetate (5.31 g) in water (13.3 mL) was added slowly. The reaction mixture was stirred for 1 h at room temperature and the aqueous layer was then extracted twice with ethyl acetate. The organic layer was dried over Na2SO4 and subjected to flash chromatography with ethylacetate to give the azo alcohol (2) as a dark oil (0.5 g, 52% yield). MS (FAB+) [M+]: calc'd for C20H20N4O3, m/z 364.4; observed, m/z 365. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | To the intermediate (G) 2.5 g (6.7 mmol) was added phosphoric acid aqueous solution (concentration 85%) 13.5 ml, and the mixture was stirred under ice-cooling for 30 minutes. In the case of maintaining ice cooling, according to the form will not be too much heat carefully dropping 40% nitrosyl sulfuric acid ester solution 2.6g (8.2 mmol), further stirred for 1 hour, to give a diazonium salt solution of intermediate (G). Under ice-cooling, the previously prepared diazonium salt solution was added to the solution <strong>[92-50-2]2-(N-ethylanilino)ethanol</strong> 2.2g (13.3 mmol) was dissolved in methanol to give 120ml of solution. After stirring for 2 hours, filter out crystallization, 1.9 g of the intermediate (H) was obtained (yield 51%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid; urea; In water; at 100℃; for 3h; | Add 1 equivalent of 2-sulfobenzaldehyde, 2 equivalents of N-Ethyl-N-hydroxyethylaniline, water, methanesulfonic acid, and 0.2 equivalent of urea to the reactor, and react at 100 for 3 hours.The resulting nonionic solid was washed with butanol and then 3 equivalents of ammonium thiosulfateAnd neutralized to obtain zwitterions-type intermediates. This was reacted with 2 equivalents of tert-butyl isocyanate in dichloromethane solvent at 40 C for 6 hours,To obtain the compound represented by the above formula (8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanesulfonic acid; urea; In water; at 100℃; for 4h; | To the reactor was added 1 equivalent of 2-sulfobenzaldehyde,1 equivalent of N-ethyl-N-hydroxyethylaniline, 1 equivalent of diethylaniline, water, methanesulfonic acid and 0.2 equivalent of urea are added and reacted at 100 C for 4 hours. The obtained nonionic solid was washed with butanol, and then 3 equivalents of ammonium thiosulfateAnd neutralized to obtain an intermediate mixture in the form of zwitterions.The ionic intermediates obtained from the column were dichloromethane (DCM)Reacted with 2 equivalents of cyclohexyl isocyanate in a solvent at 40 C for 5 hours,To obtain the compound represented by the above formula (5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; at 100℃;Inert atmosphere; | The compound of Example I (EX I) was prepared according to the following procedure. In a 1 liter pressure reactor, 250 gram of 2-(n-ethylanilino)ethanol and 0.16 gram of potassium hydroxide were added. The reactor was purged with nitrogen at 60 psi three times before adding 166 grams of ethylene oxide. The reaction mixture was stirred at about 100 C. until the pressure stabilized. Afier stripping oil any residual ethylene oxide, the product was collected as a light yellow liquid. | |
With potassium hydroxide; at 100℃; under 3102.97 Torr;Inert atmosphere; | The compound of Example I (EX I) was prepared according to the following procedure. In a 1 liter pressure reactor, 250 gram of 2-(n-ethylanilino)ethanol and 0.16 gram of potassium hydroxide were added. The reactor was purged with nitrogen at 60 psi three times before adding 166 grams of ethylene oxide. The reaction mixture was stirred at about 100 C until the pressure stabilized. After stripping off any residual ethylene oxide, the product was collected as a light yellow liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water; methanol / 3 h / 8 - 12 °C 2.1: water / 3 h / 20 - 40 °C 2.2: 35 - 40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium nitrite; In methanol; water; at 8 - 12℃; for 3h; | (1) 400ml of water, 63.5g of 30wt% (0.52mol) hydrochloric acid,20 g (0.63 mol) of methanol were mixed, and then 41.5 g (0.25 mol) of N-ethyl-N-hydroxyethylaniline was added to the mixture,Add 48 grams (0.24mol) to it after stirring well5- (N, N-di-n-propyl) amino-2-amino-1,3,4-thiadiazole, cooled to 8 C,A solution of 18 g (0.26 mol) of sodium nitrite and 40 g of water was added dropwise.As the temperature rises, the dropping temperature is controlled to 8-12 C. After the dropping,Incubate at 8-12 C for 3 hours, heat up to 95 C to recover methanol,Then draw the structural formula (XI) parent filter cake. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium nitrite; In methanol; water; at 8 - 12℃; for 2h; | (1) 500 ml of water, 97 g of 30 wt% (0.8 mol) hydrochloric acid, 30 g (0.9 mol)Methanol was mixed, and 69 g (0.42 mol) was added to the mixtureOf N-ethyl-N-hydroxyethylaniline, stir well and add 80g (0.4mol) to it5- (N, N-diisopropyl) amino-2-amino-1,3,4-thiadiazole, cooled to 8 C,Start to dropwise add a solution of 30 g (0.44 mol) of sodium nitrite and 65 g of water.As the temperature rises, the dropping temperature is controlled to 8-12 C. After the dropping,The temperature was maintained at 8-12 C for 2 hours, and the temperature was raised to 95 C to recover the methanol, and then pumped to obtain a parent cake of the structural formula (VII). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 0.17 h / Cooling with ice 1.2: 3 h / 20 °C 2.1: sodium dithionite / dimethyl sulfoxide |
Tags: 92-50-2 synthesis path| 92-50-2 SDS| 92-50-2 COA| 92-50-2 purity| 92-50-2 application| 92-50-2 NMR| 92-50-2 COA| 92-50-2 structure
[ 5521-39-1 ]
2-(4-(4-Aminophenyl)piperazin-1-yl)ethanol
Similarity: 0.92
[ 1093106-70-7 ]
N1-(2-Methoxyethyl)-N1-methylbenzene-1,3-diamine
Similarity: 0.89
[ 3077-12-1 ]
2,2'-(p-Tolylazanediyl)diethanol
Similarity: 0.87
[ 5521-39-1 ]
2-(4-(4-Aminophenyl)piperazin-1-yl)ethanol
Similarity: 0.92
[ 3077-12-1 ]
2,2'-(p-Tolylazanediyl)diethanol
Similarity: 0.87
[ 142752-12-3 ]
1-(4-Aminophenyl)piperidin-4-ol
Similarity: 0.76
[ 697306-45-9 ]
(1-Phenylpiperidin-4-yl)methanol
Similarity: 0.74
[ 5521-39-1 ]
2-(4-(4-Aminophenyl)piperazin-1-yl)ethanol
Similarity: 0.92
[ 1093106-70-7 ]
N1-(2-Methoxyethyl)-N1-methylbenzene-1,3-diamine
Similarity: 0.89
[ 3077-12-1 ]
2,2'-(p-Tolylazanediyl)diethanol
Similarity: 0.87
[ 637-31-0 ]
Bis(4-dimethylaminophenyl)amine
Similarity: 0.85
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
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.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :