Home Cart 0 Sign in  

[ CAS No. 15965-54-5 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 15965-54-5
Chemical Structure| 15965-54-5
Structure of 15965-54-5 * Storage: {[proInfo.prStorage]}

Quality Control of [ 15965-54-5 ]

Related Doc. of [ 15965-54-5 ]

SDS
Alternatived Products of [ 15965-54-5 ]
Alternatived Products of [ 15965-54-5 ]

Product Details of [ 15965-54-5 ]

CAS No. :15965-54-5 MDL No. :MFCD00051945
Formula : C8H7ClN2O Boiling Point : 365.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :182.61 g/mol Pubchem ID :519197
Synonyms :

Safety of [ 15965-54-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15965-54-5 ]

  • Downstream synthetic route of [ 15965-54-5 ]

[ 15965-54-5 ] Synthesis Path-Downstream   1~17

  • 4
  • [ 80466-79-1 ]
  • [ 15965-54-5 ]
  • [ 188027-58-9 ]
YieldReaction ConditionsOperation in experiment
The substances listed in the table which follows are also prepared by the methods given above.
  • 5
  • C4H5ClN2O3S [ No CAS ]
  • [ 15965-54-5 ]
  • [ 188027-63-6 ]
YieldReaction ConditionsOperation in experiment
The substances listed in the table which follows are also prepared by the methods given above.
  • 6
  • [ 15965-54-5 ]
  • [ 288384-91-8 ]
YieldReaction ConditionsOperation in experiment
With boron tribromide; In dichloromethane; The starting material was synthesised as follows: 2-Chloro-5-methoxybenzimidazole (0.3 g, 1.64 mmol) was suspended in dichloromethane (20 ml) under argon followed by the addition of boron tribromide (233 ul, 2.46 mmol). The reaction mixture was stirred for 2 hours at ambient temperature. The solvent was evaporated and the resulting powder was added in portions to methanol (30 ml). Silica was added and the solvent was evaporated. The resulting powder was placed on the top of a silica column and the product was eluted off using dichloromethane/methanol (95/5). Evaporation of the solvent and trituration in ether gave 2-chloro-5-hydroxybenzimidazole (440 mg, 99%).
  • 7
  • [ 37076-71-4 ]
  • [ 15965-54-5 ]
  • [ 211693-94-6 ]
YieldReaction ConditionsOperation in experiment
65% Example 33 2-Chloro-5-methoxy-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole <strong>[15965-54-5]2-Chloro-5-methoxy-1H-benzimidazole</strong> (0.661 g, 3.6 mmol) was coupled to 1,2,3-tri-O-acetyl-5deoxy-D-ribofuranose according to General Procedure II. The crude product was purified by flash chromatography (9:1 methylene chloride/ether) to yield the title compound (0.900 g, 65%) as a ~1:1 mix of regioisomers (1H NMR); MS (AP): m/z 405 (M+Na); 1H NMR (DMSO-d6) delta: 7.65-7.54 (two d, 1H), 7.21 (s, 1H), 6.97 (m, 1H), 6.18-6.11 (two d, 1H), 5.70-5.59 (m, 1H), 5.21 (q, 1H), 4.27 (m, 1H), 3.83 (two s, 3H), 2.16 (s, 3H), 2.05 (s, 3H), 1.51 (t, 3H).
  • 8
  • [ 24424-99-5 ]
  • [ 15965-54-5 ]
  • [ 256518-91-9 ]
YieldReaction ConditionsOperation in experiment
With 2-(Dimethylamino)pyridine; In acetonitrile; Preparation 21 tert-Butyl <strong>[15965-54-5]2-chloro-5-methoxy-1H-1,3-benzimidazole</strong>-1-carboxylate STR66 Di-tert-butyldicarbonate (523 mg) was added to a solution of <strong>[15965-54-5]2-chloro-5-methoxy-1H-1,3-benzimidazole</strong> (364 mg) and dimethylaminopyridine (24 mg) in acetonitrile (4 ml). The reaction mixture was stirred at room temperature for 30 minutes, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluding with a solvent gradient of 90:10 changing to 85:15, by volume, hexane:ethyl acetate to afford tert-butyl <strong>[15965-54-5]2-chloro-5-methoxy-1H-1,3-benzimidazole</strong>-1-carboxylate (470 mg) as an off-white solid, as a 1:1 mixture of regioisomers. 1 H-NMR (CDCl3)delta: 7.80 (0.5H, d), 7.55 (0.5H, d), 7.50 (0.5H, s), 7.15 (0.5H, s), 7.00 (1H, t), 3.85 (3H, s), 1.70 (9H, s).
  • 9
  • 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride [ No CAS ]
  • [ 15965-54-5 ]
  • [ 112643-46-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; thiourea; In ethanol; water; EXAMPLE 158 <strong>[15965-54-5]5-Methoxy-2-chlorobenzimidazole</strong> (0.55 g), thiourea (0.2 g) and ethanol (10 ml) were refluxed for 2 hours. To the reaction mixture was added a solution of 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.51 g) and sodium hydroxide (0.3 g) in water (5 ml) and the mixture was refluxed for 5 hours. After completion of the reaction, ethanol was distilled off and water was added to the resulting residue, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (4:1)] to give 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.62 g). NMR (CDCl3) delta: 1.60-2.00 (2H, m), 2.70 (2H, t, J=7 Hz), 2.73 (3H, s), 2.83-3.23 (2H, m), 3.73 (3H, s), 4.30 (2H, s), 6.67-7.40 (6H, m), 12.50 (1H, br.).
With sodium hydroxide; thiourea; In ethanol; water; Reference Example 52 <strong>[15965-54-5]5-Methoxy-2-chlorobenzimidazole</strong> (0.55 g), thiourea (0.2 g) and ethanol (10 ml) were refluxed for 2 hours. To the reaction mixture was added a solution of 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline hydrochloride (0.51 g) and sodium hydroxide (0.3 g) in water (5 ml) and the mixture was refluxed for 5 hours. After completion of the reaction, ethanol was distilled off and water was added to the resulting residue, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off. The resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (4:1)] to give 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.62 g). NMR (CDCl3)delta: 1.60-2.00 (2H, m), 2.70 (2H, t, J=7Hz), 2.73 (3H, s), 2.83-3.23 (2H, m), 3.73 (3H, s), 4.30 (2H, s), 6.67-7.40 (6H, m), 12.50 (1H, br.) In a manner analogous to Reference Example 52, the same compounds as those obtained in Examples numbered between 35 and 156 were produced using appropriate starting materials.
  • 10
  • [ 62000-30-0 ]
  • [ 15965-54-5 ]
  • [ 104658-72-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; thiourea; In ethanol; water; EXAMPLE 100 0.55 Gram of <strong>[15965-54-5]2-chloro-5-methoxybenzimidazole</strong>, 0.2 g of thiourea and 10 ml of ethanol were mixed together and refluxed for 2 hours. Then, 5 ml of an aqueous solution containing 0.5 g of 3-methyl-8-bromo-5,6,7,8-tetrahydroquinoline and 0.3 g of sodium hydroxide was added thereto, and the resulting mixture was refluxed for 5 hours. After the reaction was completed, ethanol was removed by evaporation, to the residue thus obtained was added water, then extracted with chloroform, the chloroform extract was dried with anhydrous magnesium sulfate, and chloroform was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to yield 0.5 g of 8-(5-methoxy-2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline in the form of colorless caramel-like substance. NMR (CDCl3) delta: 1.60-2.00 (m, 2H), 2.00-2.40 (m, 2H), 2.27 (s, 3H), 2.72 (t, 2H), 3.78 (s, 3H), 4.78 (t, 1H), 6.77 (dd, 1H), 7.00 (d, 1H), 7.22 (d, 1H), 7.40 (d, 1H), 8.23 (d, 1H).
  • 12
  • [ 15965-54-5 ]
  • potassium 4-(methoxy)phenyltrifluoroborate [ No CAS ]
  • [ 30458-48-1 ]
  • 13
  • 3-oxospiro[isobenzofuran-1(3H),4'-piperidine] hydrochloride [ No CAS ]
  • [ 15965-54-5 ]
  • [ 438191-09-4 ]
  • 14
  • 5-methoxy-2-oxo-1,3-di-tert-butoxycarbonyl-2H-benzo[d]imidazole [ No CAS ]
  • [ 15965-54-5 ]
YieldReaction ConditionsOperation in experiment
11 g With trichlorophosphate; for 3.0h;Reflux; 16 g of 5-methoxy-2-oxo-1,3-di-tert-butoxycarbonyl-2H-benzo[d]imidazole was added to 180 ml of phosphorus oxychloride, and the mixture was heated under reflux and stirred for 3 hours. Poured into ice water, added ethyl acetate, extracted and separated the organic phase, dried, concentrated, and the residue was separated on a silica gel column to obtain 11 g of 2-chloro-5-methoxy-1H-benzo[d]imidazole.
  • 15
  • [ 626-58-4 ]
  • [ 15965-54-5 ]
  • 5-methoxy-2-(4-methylpiperidin-1-yl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
7 g With potassium carbonate; In N,N-dimethyl-formamide; for 2.0h;Reflux; Add 10 g of <strong>[15965-54-5]2-chloro-5-methoxy-1H-benzo[d]imidazole</strong> to 130 ml of N,N-dimethylformamide and add 15 g of anhydrous potassium carbonate and 9 g of 4-methylpiperidine.The mixture was heated to reflux for 2 hours, cooled, and extracted with water and ethyl acetate. The organic phase was separated and concentrated. The residue was separated on a silica gel column to give 7 g of 5-methoxy-2-(4-methylpiperidine-1). -based)-1H-benzo[d]imidazole.
  • 16
  • 2-(difluoromethoxy)-7-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline [ No CAS ]
  • [ 15965-54-5 ]
  • 2-(difluoromethoxy)-5-(5-methoxy-1H-benzo[d]imidazol-2-yl)-7-methylquinoxaline [ No CAS ]
YieldReaction ConditionsOperation in experiment
27.5% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In ethanol; toluene; at 20 - 140℃; for 0.5h;Inert atmosphere; Sealed tube; Microwave irradiation; To 2-chloro-5-methoxy-1H-benzo[djimidazole (13.04 mg, 0.071 mmol) and Intermediate I-i (20 mg, 0.059 mmol) was added toluene (0.75 mL) and EtOH (0.25 mL). The reaction mixture was stirred at room temperature until solids are dissolved, then [1,1 ?-Bis(diphenylphosphino)ferrocenej dichloropalladium (II) complex with dichloromethane (1:1) (5.83 mg, 7.14 imol) was added. The flask was degassed andflushed with argon. Finally sodium carbonate (0.059 mL, 2M, 0.119 mmol) was added dropwise. The reaction vessel was sealed and bubbled with argon for 5 mm, then placed in microwave reactor at 140 C for 30 mm. The reaction mixture was cooled to room temperature and was diluted with EtOAc and water, extracted with EtOAc (3X). The combined organic layer was washed with brine, dried with Mg504 and concentrated. Thecrude sample was purified with a preparative HPLC (method A, 30-100% B in 8 mm.). The desired fractions were placed in a SpeedVac overnight to remove solvent, then lyophilized to give Example 50 (6 mg, 0.016 mmol, 27.5 % yield). ?H NMR (acetonitrile-d3, 400MHz): = 8.77 (br. s., 2H), 7.70 (s, 3H), 7.27-7.39 (m, 1H), 7.05-7.18 (m, 1H), 3.90 (s, 3H), 2.65 ppm (s, 3H). ?9F NMR (acetonitrile-d3, 376MHz):= -76.64 (br. s., 3F), -90.69 ppm (s, 2F). LC-MS: method C, RT = 1.78 mm, MS (ESI) m/z: 357.0 (M+H). Analytical HPLC purity (method A): 98%
  • 17
  • 3-(4-(mercaptomethyl)-1-phenyl-1H-pyrazol-3-yl)-2H-chromen-2-one [ No CAS ]
  • [ 15965-54-5 ]
  • 3-(4-(((6-methoxy-1H-benzo[d]imidazol-2-yl)thio)methyl)-1-phenyl-1H-pyrazol-3-yl)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 5.0h; General procedure: A mixture of 10 (5 mM), 11 (5 mM) in DMF (20 mL) containing K2CO3 (2 mM) and TBAB (2 mM) was stirred at RT for a period of 3-5 h. The reaction was monitored by TLC analysis. After the completion of reaction, the mixture was poured into ice-cold water (30 mL). The separated solid was filtered, washed with water (2 9 10 mL) and dried. The crude product was recrystallized from a suitable solvent to yield pure 9.
Historical Records

Related Functional Groups of
[ 15965-54-5 ]

Chlorides

Chemical Structure| 15965-58-9

[ 15965-58-9 ]

2-Chloro-7-methoxy-1H-benzo[d]imidazole

Similarity: 0.91

Chemical Structure| 953039-15-1

[ 953039-15-1 ]

2-Chloro-7-methoxyquinazoline

Similarity: 0.83

Chemical Structure| 886465-16-3

[ 886465-16-3 ]

2-Chloro-5-(trifluoromethoxy)-1H-benzo[d]imidazole

Similarity: 0.83

Chemical Structure| 1253654-39-5

[ 1253654-39-5 ]

2-Chloro-5-methoxyquinazoline

Similarity: 0.81

Chemical Structure| 850424-11-2

[ 850424-11-2 ]

2-Chloro-6-methoxyquinazoline

Similarity: 0.81

Ethers

Chemical Structure| 15965-58-9

[ 15965-58-9 ]

2-Chloro-7-methoxy-1H-benzo[d]imidazole

Similarity: 0.91

Chemical Structure| 4887-80-3

[ 4887-80-3 ]

5-Methoxy-1H-benzo[d]imidazole

Similarity: 0.84

Chemical Structure| 953039-15-1

[ 953039-15-1 ]

2-Chloro-7-methoxyquinazoline

Similarity: 0.83

Chemical Structure| 886465-16-3

[ 886465-16-3 ]

2-Chloro-5-(trifluoromethoxy)-1H-benzo[d]imidazole

Similarity: 0.83

Chemical Structure| 1253654-39-5

[ 1253654-39-5 ]

2-Chloro-5-methoxyquinazoline

Similarity: 0.81

Related Parent Nucleus of
[ 15965-54-5 ]

Benzimidazoles

Chemical Structure| 15965-58-9

[ 15965-58-9 ]

2-Chloro-7-methoxy-1H-benzo[d]imidazole

Similarity: 0.91

Chemical Structure| 4887-80-3

[ 4887-80-3 ]

5-Methoxy-1H-benzo[d]imidazole

Similarity: 0.84

Chemical Structure| 886465-16-3

[ 886465-16-3 ]

2-Chloro-5-(trifluoromethoxy)-1H-benzo[d]imidazole

Similarity: 0.83

Chemical Structure| 72721-02-9

[ 72721-02-9 ]

5,6-Dimethoxy-1H-benzo[d]imidazole

Similarity: 0.78

Chemical Structure| 92799-40-1

[ 92799-40-1 ]

5-Methoxy-2-methyl-1H-benzo[d]imidazole hydrochloride

Similarity: 0.77