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[ CAS No. 153259-31-5 ] {[proInfo.proName]}

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Chemical Structure| 153259-31-5
Chemical Structure| 153259-31-5
Structure of 153259-31-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 153259-31-5 ]

CAS No. :153259-31-5 MDL No. :MFCD06658231
Formula : C11H17Cl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MNVYUQSFAJMSCS-UHFFFAOYSA-N
M.W : 266.16 Pubchem ID :18792742
Synonyms :

Calculated chemistry of [ 153259-31-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.55
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 67.93
TPSA : 31.35 Ų

Pharmacokinetics

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) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.62
Log Po/w (WLOGP) : 3.19
Log Po/w (MLOGP) : 1.4
Log Po/w (SILICOS-IT) : 3.37
Consensus Log Po/w : 2.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.02
Solubility : 0.253 mg/ml ; 0.00095 mol/l
Class : Soluble
Log S (Ali) : -2.93
Solubility : 0.314 mg/ml ; 0.00118 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.52
Solubility : 0.00798 mg/ml ; 0.00003 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.27

Safety of [ 153259-31-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P270-P271-P264-P280-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:3261
Hazard Statements:H302+H312+H332-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 153259-31-5 ]

* 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.

  • Downstream synthetic route of [ 153259-31-5 ]

[ 153259-31-5 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 153259-31-5 ]
  • [ 924663-39-8 ]
YieldReaction ConditionsOperation in experiment
99% With 3-chloro-benzenecarboperoxoic acid In methanol; dichloromethane for 1h;
72% Stage #1: 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride With sodium hydrogencarbonate In chloroform Stage #2: With 3-chloro-benzenecarboperoxoic acid at 5℃; for 2.41667h; Further stages.;
71% Stage #1: 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride With ammonia; water In chloroform for 0.166667h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In chloroform at 35℃; for 2.5h;
  • 2
  • [ 153259-31-5 ]
  • [ 924663-38-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium bicarbonate / CHCl3 1.2: 72 percent / m-chloroperbenzoic acid / 2.42 h / 5 °C 2.1: 96 percent / potassium carbonate / dimethylformamide / 20 °C 3.1: m-chloroperbenzoic acid / CH2Cl2 / 2.67 h / 0 °C
Multi-step reaction with 3 steps 1: 99 percent / 3-chloroperbenzoic acid / CH2Cl2; methanol / 1 h 2: 46 percent / triethylamine / acetonitrile / 2 h / 20 °C 3: 35 percent / aq. potassium hydrogencarbonate; 3-chloroperbenzoic acid / CH2Cl2 / 2 h / 0 °C
  • 3
  • [ 153259-31-5 ]
  • [ 924663-40-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium bicarbonate / CHCl3 1.2: 72 percent / m-chloroperbenzoic acid / 2.42 h / 5 °C 2.1: 96 percent / potassium carbonate / dimethylformamide / 20 °C
Multi-step reaction with 2 steps 1: 99 percent / 3-chloroperbenzoic acid / CH2Cl2; methanol / 1 h 2: 46 percent / triethylamine / acetonitrile / 2 h / 20 °C
  • 4
  • [ 153259-31-5 ]
  • [ 924663-37-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium bicarbonate / CHCl3 1.2: 72 percent / m-chloroperbenzoic acid / 2.42 h / 5 °C 2.1: 96 percent / potassium carbonate / dimethylformamide / 20 °C 3.1: m-chloroperbenzoic acid / CH2Cl2 / 2.67 h / 0 °C
Multi-step reaction with 3 steps 1: 99 percent / 3-chloroperbenzoic acid / CH2Cl2; methanol / 1 h 2: 46 percent / triethylamine / acetonitrile / 2 h / 20 °C 3: 51 percent / aq. sodium carbonate; peracetic acid / CH2Cl2 / 52 h / 20 °C
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 24 h / 23 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 23 °C / Cooling with acetone-dry ice
  • 5
  • 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride [ No CAS ]
  • [ 134469-07-1 ]
  • [ 117976-90-6 ]
YieldReaction ConditionsOperation in experiment
Example 2 Preparation of 2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridinyl]methyl]-sulfinyl]-lH-benzimidazole sodium (Rabeprazole Sodium) 2-Mercapto benzimidazole (15 g) was suspended in 500 ml Purified water and Sodium hydroxide (8 g). To this was slowly added about 25 g of 2-Chloromethyl- 3-methyl-4-(methoxy propoxy)pyridine hydrochloride. The reaction mass was stirred for 2 hours at 20 - 30 C and solids were filtered to obtain 2-[[[4-(3- methoxy-propoxy)-3-methyl-2-pyridinyl]methyl]-thio]-lH-benzimidazole.The above wet material was suspended in 700 ml Purified Water, Sodium hydroxide (8 g) and Pyridine (17.0 ml). To this 215 g of sodium hypochlorite solution having a chlorine content of 3.2% was slowly added at 5- 10 C in 2 hours. The reaction mass was maintained at 5 - 8 C for 2 - 4 hours. After completion of the reaction, excess sodium hypochlorite was decomposed using EPO <DP n="10"/>5% aqueous sodium thiosulphate solution. The reaction mass was saturated with about 210 gm of sodium chloride and extracted with 300 ml of dichloromethane twice. The organic layer was dried over Sodium sulphate and concentrated under vacuum to yield a residue.To this residue, about 200 ml of Ethyl acetate was added and heated to 45 - 50 C for 30 mins for dissolution. This solution was then added slowly to about 600ml of n-Heptane under stirring, filtered under nitrogen atmosphere, washed with 30 ml of n-Heptane and dried in an oven at 45-50 C to give 28.0 g of the title compound.
  • 6
  • 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride [ No CAS ]
  • [ 134469-07-1 ]
  • [ 117977-21-6 ]
YieldReaction ConditionsOperation in experiment
96.8% With triethylamine; In acetonitrile; at 23℃; for 24h; Analytical grade 250 mL of acetonitrile and 15.0 g (0.1 mol) of 2-mercaptobenzimidazole were added to the three-necked flask at room temperature. 13.3 g (0.05 mol) of 2-chloromethyl-3-methyl-4-(3-methoxypropoxy)pyridine hydrochloride and 13 mL of triethylamine were added and stirred at room temperature for 24 h. The reaction solution was evaporated to dryness, and then 50 mL of dichloromethane and 50 mL of water were successively added, and the mixture was shaken, and the mixture was allowed to stand for separation to obtain an organic dichloromethane layer. After evaporating to dryness, 16.6 g of a thioether compound was obtained in a yield of 96.8%.
89.3% With sodium hydroxide; In ethanol; at 68℃; for 4h; 2-Chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride (0.50 g, 1.88 mmol) was placed in a 125 ml eggplant-shaped flask, and 11 ml of ethanol was added to dissolve it.Further, 1H-benzimidazole-2-thiophenol (0.28 g, 1.88 mmol) and 4 ml of NaOH (80 g/L) were added, and refluxed at 68 C for 4 hr. Pour the reaction solution into a 100 ml beaker.Naturally cooled to room temperature, a white solid precipitated.Recrystallization of ethyl acetate and petroleum ether (2:1) gave white needle crystals0.58 g, yield 89.3%.
With sodium hydroxide; In water; at 20 - 30℃; for 2h; Example 1 :Preparation of 2-[[[4-(3-methoxy propoxy)-3-methyl-2-pyridinyl]methyl]- thio]-lH-benzimidazole (Rabeprazole Sulphide).2-Mercapto benzimidazole (15 g) was suspended in 500 ml Purified water and Sodium hydroxide (8 g). To this was slowly added about 25 g of 2-Chloromethyl -3-methyl-4-(methoxy propoxy)pyridine hydrochloride. The reaction mass was stirred for 2 hours at 20 - 30 C and solids were filtered and the wet material can be directly taken up for oxidation or optionally dried in an oven at 45-50 C to give 31 gm of the title compound.
With sodium hydroxide; In methanol; at 50 - 60℃; for 4.5h; The condensation reaction: In a first preparation tank into a clean reaction 32.6kg of methanol, stirred at a rotation speed of 35Hz, of 2-chloro-3-methyl-4-methoxy-propoxy pyridine hydrochloride 25.00kg, stirring It was dissolved to prepare a 2-chloro-3-methyl-4-methanol solution methoxypropoxy pyridine hydrochloride standby.In the second reaction tank clean methanol was prepared 98.8kg, at 40Hz rotational speed of sodium hydroxide was added under stirring 8.15kg, 20-25 temperature after mixing of 2-mercaptobenzimidazole 14.11kg, warmed to 50-60 , temperature 50-60 deg.] C was added the above prepared 2-chloro-3-methyl-4-methoxy-propoxy pyridine hydrochloride in methanol, adding about 30min completed.Maintaining the temperature and the reaction was continued 4h, 2-chloromethyl-phase detection methyl-4-methoxypropoxy pyridine hydrochloride residue is not greater than 0.5%, the reaction was terminated, and filtered.5.4kg washed with methanol and the combined filtrate and the washings, temperature 40-50 deg.] C, and concentrated in vacuo to a reduced pressure of -0.08 ~ -0.1Mpa methanol-free effluent, 66.3kg of methylene chloride was added, washed with 87.5kg of purified water was added and stirred to dissolve a the organic phase left, the aqueous phase was added 8.3kg of dichloromethane, washed once, treated with waste water, the combined organic phases washed with 62.4kg of purified water was added, the waste water phase, the organic phase in the temperature 25 ~ 30 , the degree of vacuum -0.08 ~ -0.1Mpa distillation under reduced pressure to stop the precipitated solid was distilled, petroleum ether was added dropwise with stirring 33.0kg crystallization, crystal growing temperature 0-5 deg.] C for 3 hours by centrifugation, washed, and dried, to obtain rabeprazole sulfide.Table 1 gives the amount of raw materials and a condensation reaction.

  • 7
  • [ 153259-31-5 ]
  • [ 149-30-4 ]
  • [ 117976-20-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In ethanol 92 2-{4-(3-Methoxypropoxy)-3-methylpyridine-2-yl}methylthio-benzothiazole STR168 EXAMPLE 92 2-{4-(3-Methoxypropoxy)-3-methylpyridine-2-yl}methylthio-benzothiazole STR168 A mixture comprising 0.8 g of 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride, 0.5 g of 2-mercaptobenzothiazole, 0.36 g of sodium hydroxide and 30 ml of ethanol was stirred at a room temperature for 6 hours and distilled under a reduced pressure to remove the ethanol. The residue was purified by silica gel column chromatography to obtain 0.85 g of the title compound as a pale yellow crystal. 1 H-NMR(CDCl3) δ; 1.9~2.2(m, 2H), 2.30(s, 3H), 3.35(s, 3H), 3.56(t, J=6.1 Hz, 2H), 4.10(t, J=6.1 Hz, 2H), 4.81(s, 2H), 6.70(d, J=5.7 Hz, 1H), 7.1~7.5(m, 2H), 7.5~7.9(m, 2H), 8.29(d, J=5.7 Hz, 1H).
  • 8
  • [ 153259-31-5 ]
  • [ 583-39-1 ]
  • [ 1114543-47-3 ]
YieldReaction ConditionsOperation in experiment
79% With sodium hydroxide In water at 15 - 75℃;
  • 9
  • 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride [ No CAS ]
  • [ 117976-89-3 ]
  • [ 935260-92-7 ]
  • 10
  • [ 153259-31-5 ]
  • [ 1322643-80-0 ]
  • [ 1322643-81-1 ]
YieldReaction ConditionsOperation in experiment
85.4% With potassium carbonate In methanol at 20 - 30℃; 1.1 Step 1: 2-[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methylthio]-6,7-dihydro-3H-benzofuro[5 Preparation of ,6-d]imidazole (Compound (IV)) Methanol (1630ml) was added to the reactor, the hydrochloride of compound (III) (206.8g, 0.78mol) and potassium carbonate (195.2g, 1.42mol) were added under stirring, and the temperature was controlled to 2030°C,Compound (II) (135.8 g, 0.71 mol) was added, and the reaction was carried out for 10-30 h. HPLC detection,The reaction is complete. The reaction system was heated to 30-40°C, and the solvent was concentrated.Pure water (1630 ml) was added to the system, followed by stirring for 2-3 hours. filter, collect the filter cake,Wet product samples.The filter cake was transferred to the reactor, acetonitrile (3260ml) was added, the temperature was refluxed until the sample was completely dissolved, and the target compound (232.6g) was obtained by cooling, crystallization, filtration, acetonitrile washing and drying, with a yield of 85.4% and a purity of 99.61%. .
70.1% With sodium hydroxide In methanol for 3h; 14.5 Step 5: Preparation of 2-[[4-(3-methoxylpropoxy)-3-methyl-2-pyridyl] methylsulfo]-6,7-dihydro-3H-benzofuro[5,6-d]imidazole [Show Image] A solution of 2-chloromethyl-4-(3-methoxylpropoxy)-3-methylpyridine hydrochloride(26.6 g, 0.1 mol) and anhydrous methanol (100mL) was added dropwise to a mixture of the product as obtained in the Step 4 (19.2 g, 0.1 mol), sodium hydroxide (8 g, 0.2 mol) and anhydrous methanol (100mL), after the end of dropwise addition, the agitation was kept for 3 h, then concentrated, filtered, washed with water, dried and recrystallized to obtain a product (27 g, 70.1 %).
  • 11
  • 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride [ No CAS ]
  • [ 5747-48-8 ]
  • C28H32N4O2S [ No CAS ]
  • 12
  • [ 37699-43-7 ]
  • [ 153259-31-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / Reflux 2: sodium hydroxide 3: acetic acid / methanol; toluene 4: sodium hydroxide / methanol 5: thionyl chloride
  • 13
  • [ 59886-90-7 ]
  • 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydroxide 2: acetic acid / methanol; toluene 3: sodium hydroxide / methanol 4: thionyl chloride
  • 14
  • [ 117977-18-1 ]
  • [ 153259-31-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid / methanol; toluene 2: sodium hydroxide / methanol 3: thionyl chloride
Multi-step reaction with 3 steps 1: trifluorormethanesulfonic acid / 5 h / 30 °C 2: sodium hydroxide; water / 1 h / 80 °C / pH 14 3: thionyl chloride / ethyl acetate / 3 h / 5 - 20 °C
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / 3 h / 50 °C 2: sodium hydroxide; water / 1 h / 80 °C / pH 14 3: thionyl chloride / ethyl acetate / 3 h / 5 - 20 °C
  • 15
  • [ 117977-19-2 ]
  • [ 153259-31-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol 2: thionyl chloride
Multi-step reaction with 2 steps 1: sodium hydroxide; water / 1 h / 80 °C / pH 14 2: thionyl chloride / ethyl acetate / 3 h / 5 - 20 °C
  • 16
  • [ 675198-19-3 ]
  • 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride [ No CAS ]
  • 17
  • [ 153259-31-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / methanol / 5 h / Reflux 2.1: diethyl (2S,3S)-tartrate; titanium propoxide / water; toluene / 1 h / 80 °C 2.2: 1.5 h / 30 °C
  • 18
  • [ 153259-31-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / methanol / 5 h / Reflux 2.1: diethyl (2R,3R)-tartrate; titanium propoxide / water; toluene / 1 h / 80 °C 2.2: 1.5 h / 30 °C
  • 19
  • [ 153259-31-5 ]
  • [ 106-49-0 ]
  • [ 2201817-55-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide; sodium iodide / acetonitrile / 24 h / Reflux 2: copper(II) bis(trifluoromethanesulfonate); N,N-bis(pyridin-2-ylmethyl)benzenamine; oxygen; potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 24 h / 20 °C / 760.05 Torr / Sealed tube
  • 20
  • [ 153259-31-5 ]
  • [ 106-49-0 ]
  • [ 2201817-61-8 ]
YieldReaction ConditionsOperation in experiment
78% With sodium iodide; sodium hydroxide In acetonitrile for 24h; Reflux;
  • 21
  • [ 153259-31-5 ]
  • [ 117976-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / acetonitrile / 24 h / 23 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 23 °C / Cooling with acetone-dry ice 3: iron; acetic acid / water / 24 h / 95 °C
  • 22
  • 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride [ No CAS ]
  • [ 1849-36-1 ]
  • 4-(3-methoxypropoxy)-3-methyl-2-[(4-nitrophenyl)thio]methyl}pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.3% With sodium hydroxide In ethanol; water at 20℃; for 6h; 1.A Preparation of 4-(3-methoxypropoxy)-3-methyl-2-[(4-nitrophenyl)thio]methyl}pyridine 4-Nitrothiophenol (15.52 g, 0.10 mol) was added to a 500 mL eggplant-shaped flask.2-Chloromethyl-3-methyl-4-(methoxypropoxy)pyridine hydrochloride (26.62 g, 0.10 mol) and dry ethanol (200 mL).A 3 mol/L aqueous sodium hydroxide solution (100 mL) was added dropwise at room temperature.After the completion of the dropwise addition, the reaction was carried out at room temperature for 6 hours. After the reaction,Part of the ethanol was distilled off under reduced pressure, and 200 mL of water was added to the residue to precipitate a large amount of white solid.After suction filtration, the filter cake was washed with water and dried in the air to obtain a white solid 31.81 g.The yield was 91.3%. The product was used in the next step without further purification.
89.7% With sodium hydroxide In ethanol; water at 20℃; for 8h; 3.1.1. General Procedure for the Preparation of 2-[(4-nitrophenyl)thio]methyl}pyridineDerivatives (3a-3d) General procedure: 4-Nitrobenzenethiol 1 (1.55 g, 0.01 mol), and 2-(chloromethyl)pyridine hydrochloride derivatives 2(0.01 mol) were dissolved in EtOH (100 mL), then aqueous NaOH (2M) was added dropwise. After theaddition completed, the solution was stirred for 8 h at room temperature. Upon completion, the excessethanol was evaporated to give the residue. A large number of white solids have been precipitatedwhen 200 mL of water was added. The Precipitate was filtered o and washed with water to obtain theintermediates (3a-3d), which was used for next step without further purification.
  • 23
  • [ 153259-31-5 ]
  • [ 2374270-86-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 8 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 3: chloroform / 20 °C
  • 24
  • [ 153259-31-5 ]
  • [ 2374270-89-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 8 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 3: chloroform / 20 °C
  • 25
  • [ 153259-31-5 ]
  • [ 2374270-91-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 8 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 3: chloroform / 20 °C
  • 26
  • [ 153259-31-5 ]
  • [ 2374270-93-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 8 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 3: chloroform / 20 °C
  • 27
  • [ 153259-31-5 ]
  • [ 2374270-80-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 8 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr
  • 28
  • [ 153259-31-5 ]
  • [ 2374270-84-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 8 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 3: chloroform / 20 °C
  • 29
  • [ 153259-31-5 ]
  • [ 100-02-7 ]
  • [ 2407783-11-1 ]
YieldReaction ConditionsOperation in experiment
92.6% With sodium hydroxide In ethanol; water at 20℃; for 6h; 1.A Step A: Preparation of 4-(3-methoxypropoxy)-3-methyl-2-[(4-nitrophenoxy)methyl]pyridine Add 4-nitrophenol (13.91g, 0.10mol) to a 500mL eggplant-shaped bottle.2-chloromethyl-3-methyl-4-(3-methoxypropoxy)pyridine hydrochloride (26.62 g, 0.10 mol) and absolute ethanol (200 mL). A 3mol/L sodium hydroxide aqueous solution (100 mL) was added dropwise at room temperature.After the dropwise addition was completed, the reaction was performed at room temperature for 6 hours. After the reaction, a portion of the ethanol was distilled off under reduced pressure.200 mL of water was added to the residue, and a large amount of white solid was precipitated. The solution was filtered with suction, and the filter cake was washed with water.It was left to dry in the air to obtain 30.68 g of a white solid with a yield of 92.6%.The product was used directly in the next step without further purification.
  • 30
  • [ 153259-31-5 ]
  • [ 2407783-12-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 6 h / 20 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 5 h / 20 °C
  • 31
  • [ 153259-31-5 ]
  • [ 2407782-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water / 6 h / 20 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 5 h / 20 °C 3: dichloromethane / 2 h / 20 °C
  • 32
  • [ 118175-10-3 ]
  • 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.7% With thionyl chloride; In ethyl acetate; at 5 - 20℃; for 3.0h; Take 40 g of <strong>[118175-10-3]3-methyl-2-hydroxymethyl-4-(3-methoxypropoxy)pyridine</strong> prepared according to Example 2.Add 80 g of ethyl acetate and stir evenly, then cool to 5C, add 27.3 g of thionyl chloride dropwise, and finish dropping in about 1 hour.After dripping, the temperature was raised to room temperature and reacted for 2 hours, and a large amount of solid materials were precipitated.Filter, rinse the filter cake with an appropriate amount of ethyl acetate, and dry it after discharging to obtain the title compound with a molar yield of 95.7% and a purity of 99.94%.
  • 33
  • [ 153259-31-5 ]
  • [ 1807320-35-9 ]
  • [ 2098021-68-0 ]
YieldReaction ConditionsOperation in experiment
51% With potassium carbonate In acetonitrile Reflux;
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(4-Methoxy-3-methylpyridin-2-yl)methanol

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