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[ CAS No. 27231-36-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 27231-36-3
Chemical Structure| 27231-36-3
Chemical Structure| 27231-36-3
Structure of 27231-36-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 27231-36-3 ]

CAS No. :27231-36-3 MDL No. :MFCD00010617
Formula : C8H8N2S Boiling Point : -
Linear Structure Formula :- InChI Key :CWIYBOJLSWJGKV-UHFFFAOYSA-N
M.W : 164.23 Pubchem ID :712373
Synonyms :

Calculated chemistry of [ 27231-36-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.31
TPSA : 67.48 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) : -5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 2.16
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 2.76
Consensus Log Po/w : 1.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.339 mg/ml ; 0.00206 mol/l
Class : Soluble
Log S (Ali) : -2.98
Solubility : 0.171 mg/ml ; 0.00104 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.4
Solubility : 0.0655 mg/ml ; 0.000399 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.13

Safety of [ 27231-36-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 27231-36-3 ]

* 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 [ 27231-36-3 ]

[ 27231-36-3 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 39267-05-5 ]
  • [ 27231-36-3 ]
  • 3,10-dimethyl-benzo[4',5']imidazo[2',1':2,3]thiazolo[4,5-<i>b</i>]quinoxaline [ No CAS ]
  • 2
  • [ 2379-60-4 ]
  • [ 27231-36-3 ]
  • 10-methyl-2-nitro-benzo[4',5']imidazo[2',1':2,3]thiazolo[4,5-<i>b</i>]quinoxaline [ No CAS ]
  • 3
  • [ 2958-87-4 ]
  • [ 27231-36-3 ]
  • 3-chloro-10-methyl-benzo[4',5']imidazo[2',1':2,3]thiazolo[4,5-<i>b</i>]quinoxaline [ No CAS ]
  • 4
  • [ 75-03-6 ]
  • [ 27231-36-3 ]
  • [ 106039-67-2 ]
YieldReaction ConditionsOperation in experiment
With DBN In N,N-dimethyl-formamide at 45 - 55℃; for 14h;
  • 5
  • [ 140-89-6 ]
  • [ 496-72-0 ]
  • [ 27231-36-3 ]
YieldReaction ConditionsOperation in experiment
85% In ethanol; water monomer for 8h; Heating;
81% With water monomer In ethanol at 80℃; for 16h; Sealed tube; 2.3.1 Preparation of 5-methyl-2-thiobenzimidazole (3) To a 10 mL microwave vial was added 5-methyl-1,2-diaminobenzene (181 mg, 1.5 mmol) and potassium ethyl xanthogenate (285 mg, 1.8 mmol, 1.2 equiv).2 mL ethanol was added, followed by 1 mL water and the mixture was sonicated for 10 min until only a fine powder remained. The vial was capped and crimped and the reaction was then placed in an 80 °C bath and heated for 16 h. The vial was then allowed to cool to room temperature and water (15 mL) was added. A white solid precipitated. The pH of the solution was adjusted to ca.5 (some solid dissolved) and the solution was filtered and the residue was washed with water (2 x 30 mL). The residue was then dried under airflow to afford a white solid.198 mg, 81%.1H NMR (300 MHz, DMSO-d6) δ 12.78 - 11.90 (br s, 2H), 7.08 - 6.99 (m, 1H), 6.94 (d, J = 8.1 Hz, 2H), 2.34 (s, 3H). Spectral data are in agreement with the literature. Mavrova et al., 2015.
81% With water monomer In ethanol at 80℃; for 16h; Sealed tube; 2.3.1 Preparation of 5-methyl-2-thiobenzimidazole (3) To a 10 mL microwave vial was added 5-methyl-1,2-diaminobenzene (181 mg, 1.5 mmol) and potassium ethyl xanthogenate (285 mg, 1.8 mmol, 1.2 equiv).2 mL ethanol was added, followed by 1 mL water and the mixture was sonicated for 10 min until only a fine powder remained. The vial was capped and crimped and the reaction was then placed in an 80 °C bath and heated for 16 h. The vial was then allowed to cool to room temperature and water (15 mL) was added. A white solid precipitated. The pH of the solution was adjusted to ca.5 (some solid dissolved) and the solution was filtered and the residue was washed with water (2 x 30 mL). The residue was then dried under airflow to afford a white solid.198 mg, 81%.1H NMR (300 MHz, DMSO-d6) δ 12.78 - 11.90 (br s, 2H), 7.08 - 6.99 (m, 1H), 6.94 (d, J = 8.1 Hz, 2H), 2.34 (s, 3H). Spectral data are in agreement with the literature. Mavrova et al., 2015.
  • 7
  • [ 125163-08-8 ]
  • [ 27231-36-3 ]
  • [ 104658-76-6 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide In methanol; water for 1h; Heating;
  • 8
  • [ 353-83-3 ]
  • [ 27231-36-3 ]
  • [ 105771-14-0 ]
YieldReaction ConditionsOperation in experiment
58% With DBN In N,N-dimethyl-formamide at 45 - 55℃; for 14h;
  • 9
  • 1-(2-chloroethyl)-2-methyl-5-nitro-1H-imidazole hydrochloride [ No CAS ]
  • [ 27231-36-3 ]
  • 5-Methyl-2-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethylsulfanyl]-1H-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In acetone for 20h; Heating;
  • 10
  • [ 114060-09-2 ]
  • [ 27231-36-3 ]
  • [ 106746-94-5 ]
YieldReaction ConditionsOperation in experiment
73% In ethanol for 2h;
  • 11
  • [ 27231-36-3 ]
  • potassium 5-methylbenzimidazole-2-sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With KO2 In pyridine at 60℃; for 6h;
  • 12
  • [ 67-56-1 ]
  • [ 27231-36-3 ]
  • [ 614-97-1 ]
  • 5-methyl-2-methoxybenzimidazole [ No CAS ]
  • 13
  • [ 107-10-8 ]
  • [ 27231-36-3 ]
  • [ 614-97-1 ]
  • 5-methyl-2-(propylamino)benzimidazole [ No CAS ]
  • 14
  • [ 75-04-7 ]
  • [ 27231-36-3 ]
  • [ 614-97-1 ]
  • N-ethyl-5-methyl-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 15
  • [ 27231-36-3 ]
  • [ 109-73-9 ]
  • [ 614-97-1 ]
  • 5-methyl-2-(butylamino)benzimidazole [ No CAS ]
  • 16
  • [ 27231-36-3 ]
  • [ 614-97-1 ]
  • [ 6285-68-3 ]
  • 18
  • [ 75-15-0 ]
  • [ 496-72-0 ]
  • [ 27231-36-3 ]
YieldReaction ConditionsOperation in experiment
90% With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In neat (no solvent) at 20℃; for 0.5h; General procedure: The basic procedure for preparing all products was similar. Taking the entry 1 inTable 2 as an example: 1a (2 mmol) and [DBUH][OAc] (1 mL) were added to a 10mLflask and stirred at room temperature. After 30 minutes, adding 5mL water into theflask dispersed the solid product, which could be separated by filtration. The solid wasrecrystallized from an ethyl acetate and petroleum ether mixture (v/v, 1/1) to get 2a.The aqueous residue was evaporated under vacuum at 50C for 8 h and reused in thenext run. All the products were known compounds, and the characteristic data accordedwith the relevant literature.
86% With potassium hydroxide In N,N-dimethyl acetamide for 0.0416667h; Irradiation;
With potassium hydroxide In methanol; water
With sodium hydroxide In ethanol; water Reflux;
With potassium hydroxide In water at 70℃;

  • 19
  • [ 4897-25-0 ]
  • [ 27231-36-3 ]
  • 5-Methyl-2-(3-methyl-5-nitro-3H-imidazol-4-ylsulfanyl)-1H-benzoimidazole [ No CAS ]
  • 21
  • [ 27231-36-3 ]
  • [ 6285-68-3 ]
YieldReaction ConditionsOperation in experiment
63% With ammonia; ozone In dichloromethane at 25℃;
  • 22
  • 2-chloromethyl-3,5-dimethylpyridine hydrochloride [ No CAS ]
  • [ 27231-36-3 ]
  • 2-(3,5-Dimethyl-pyridin-2-ylmethylsulfanyl)-5-methyl-1H-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydroxide In methanol Heating;
  • 23
  • [ 698-80-6 ]
  • [ 27231-36-3 ]
  • 2-(3,4-difluoro-benzylsulfanyl)-6-methyl-1<i>H</i>-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: 2-mercapto-5-methylbenzimidazole With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 4-(chloromethyl)-1,2-difluorobenzene In methanol; N,N-dimethyl-formamide at 20℃;
  • 24
  • [ 75462-59-8 ]
  • [ 27231-36-3 ]
  • 2-(3,5-bis-trifluoromethyl-benzylsulfanyl)-6-methyl-1<i>H</i>-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 2-mercapto-5-methylbenzimidazole With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 3,5-bis(trifluoromethyl)benzyl chloride In methanol; N,N-dimethyl-formamide at 20℃;
  • 25
  • [ 64407-07-4 ]
  • [ 27231-36-3 ]
  • [ 449813-41-6 ]
  • 26
  • [ 68220-26-8 ]
  • [ 27231-36-3 ]
  • 2-(2-chloro-6-fluoro-benzylsulfanyl)-6-methyl-1<i>H</i>-benzoimidazole [ No CAS ]
  • 27
  • [ 1958-93-6 ]
  • [ 27231-36-3 ]
  • 2-(2-fluoro-6-nitro-benzylsulfanyl)-6-methyl-1<i>H</i>-benzoimidazole [ No CAS ]
  • 28
  • [ 74367-78-5 ]
  • [ 27231-36-3 ]
  • 2-(3,5-dinitro-benzylsulfanyl)-6-methyl-1<i>H</i>-benzoimidazole [ No CAS ]
  • 30
  • [ 86-52-2 ]
  • [ 27231-36-3 ]
  • 5-methyl-2-(1-naphthylmethylsulfanyl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 5-methyl-1H-benzoimidazole-2-thiol With sodium In methanol; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 1-Chloromethylnaphthalene In methanol; N,N-dimethyl-formamide at 20℃;
  • 31
  • [ 6125-37-7 ]
  • [ 27231-36-3 ]
  • 4-methyl-2-[2-(5-methyl-1<i>H</i>-benzoimidazol-2-ylsulfanyl)-acetylamino]-thiazole-5-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In acetone for 8h; Heating;
  • 32
  • [ 10254-07-6 ]
  • [ 27231-36-3 ]
  • <i>N</i>-benzhydryl-2-(5-methyl-1<i>H</i>-benzoimidazol-2-ylsulfanyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In acetone at 20℃; for 8h;
  • 33
  • [ 1822-51-1 ]
  • [ 27231-36-3 ]
  • 5-methyl-2-(4-pyridylmethylsulfanyl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: 5-methyl-1H-benzoimidazole-2-thiol With sodium In methanol; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 4-picolylchloride hydrochloride In methanol; N,N-dimethyl-formamide at 20℃;
  • 34
  • [ 6959-48-4 ]
  • [ 27231-36-3 ]
  • 5-methyl-2-(3-pyridylmethylsulfanyl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 5-methyl-1H-benzoimidazole-2-thiol With sodium In methanol; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 3-chloromethylpyridinium chloride In methanol; N,N-dimethyl-formamide at 20℃;
  • 35
  • [ 27231-36-3 ]
  • [ 50772-54-8 ]
  • <i>N</i>-(4,5-dimethyl-thiazol-2-yl)-2-(5-methyl-1<i>H</i>-benzoimidazol-2-ylsulfanyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate In acetone for 8h; Heating;
  • 36
  • [ 75-15-0 ]
  • [ 496-72-0 ]
  • [ 27231-36-3 ]
YieldReaction ConditionsOperation in experiment
71.3% With sodium hydroxide In ethanol Reflux;
55.8% With sodium hydroxide In ethanol; water at 0℃; for 5h; Reflux; 1.1 1. Synthesis of 5-methyl-1H-benzo[d]imidazole-2-thiol [5-methyl-1H-benzo[d]imidazole-2-thiol](8) 3,4-diaminotoluene (65.48 mmol, 8.0 g) was added to water (12 mL), ethanol (80 mL), sodium hydroxide (NaOH) (1.16 eq, 3.03g).Divide into the mixed solution little by little. Carbon disulfide (CS2) (1.16 equivalent, 4.58 mL) was slowly added dropwise at 0° C. to the reaction mixture, followed by refluxing for 5 hours. After the reaction mixture is cooled to room temperature, charcoal is added little by little, and then refluxed for 10 minutes. Hot water is poured into the reaction mixture, and the insoluble solid is filtered off. The filtrate is treated with 50% acetic acid and stored in a refrigerator. The resulting solid was filtered and washed with an excess of water to obtain compound 8.Brown solid; Reaction time 5 hours; Yield 55.8%;
With sodium hydroxide In ethanol; water for 3h; Heating;
In ethanol at 20℃; for 120h; 47.a (47a) 5-methyl-1H-benzimidazole-2-thiol First, 3-amino-4-nitrotoluene (6.3 g, 41.4 mmol) and 10% palladium carbon (900 mg) were suspended in methanol (70 ml) and the mixture was stirred in a hydrogen atmosphere for 3 hours. The reaction vessel was purged with nitrogen and a catalyst was removed by filtration and washed with ethanol. To the reaction mixture, carbon disulfide (20 ml) was added and the mixture was stirred at room temperature for 5 days. After the reaction mixture was concentrated, diethyl ether was added to the residue. The generated solid was collected by filtration to obtain the title compound (6.1 g, yield: 89.7%) was obtained as a light yellow solid. 1H NMR(400 MHz, DMSO-d6) δppm; 2.33(3H, s), 6.90-6.93(2H, m), 7.00(1H, d, J=8 Hz).
With sodium hydroxide In ethanol; water Reflux;
With potassium hydroxide In ethanol for 8h; Reflux;
In water at 60℃; for 12h;

  • 37
  • [ 60442-41-3 ]
  • [ 27231-36-3 ]
  • 2-[2-(5-methyl-1<i>H</i>-benzoimidazol-2-ylsulfanyl)-acetylamino]-4,5,6,7-tetrahydro-benzo[<i>b</i>]thiophene-3-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate In acetone for 2h; Heating;
  • 38
  • [ 100-39-0 ]
  • [ 27231-36-3 ]
  • 1-benzyl-2-(benzylthio)-5-methyl-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 39
  • [ 102-92-1 ]
  • [ 27231-36-3 ]
  • 8-methyl-2-phenyl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-one [ No CAS ]
  • 8-methyl-4-phenyl-3,4-dihydro-2H-[1,3]thiazino[3,2-a]benzimidazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 48% 2: 33% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 40
  • [ 98-88-4 ]
  • [ 27231-36-3 ]
  • 1-benzoyl-5-methyl-1H-benzimidazole-2-thiol [ No CAS ]
  • S-(1-benzoyl-5-methyl-1H-benzimidazol-2-yl)benzenecarbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 51% 2: 32% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 41
  • [ 122-01-0 ]
  • [ 27231-36-3 ]
  • 1-(4-chlorobenzoyl)-5-methyl-1H-benzimidazole-2-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 42
  • [ 105-36-2 ]
  • [ 27231-36-3 ]
  • ethyl [(5-methyl-1H-benzimidazol-2-yl)thio]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 43
  • [ 75-36-5 ]
  • [ 27231-36-3 ]
  • [ 21541-33-3 ]
YieldReaction ConditionsOperation in experiment
64% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 44
  • [ 79-04-9 ]
  • [ 27231-36-3 ]
  • [ 79938-36-6 ]
YieldReaction ConditionsOperation in experiment
64% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 45
  • [ 109-64-8 ]
  • [ 27231-36-3 ]
  • 8-methyl-3,4-dihydro-2H-[1,3]thiazino[3,2-a]benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 46
  • [ 625-36-5 ]
  • [ 27231-36-3 ]
  • 8-methyl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 47
  • [ 75-26-3 ]
  • [ 27231-36-3 ]
  • 2-(isopropylthio)-5-methyl-1H-benzimidazole [ No CAS ]
  • 1-isopropyl-2-(isopropylthio)-5-methyl-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 42% 2: 33% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 48
  • [ 2632-13-5 ]
  • [ 27231-36-3 ]
  • 1-(4-methoxyphenyl)-2-[(5-methyl-1H-benzimidazol-2-yl)thio]ethanone [ No CAS ]
  • 1-(4-methoxyphenyl)-2-({1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-benzimidazol-2-yl}thio)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 48% 2: 32% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 49
  • 6-(chloromethyl)pyrimidin-4(3H)-one [ No CAS ]
  • [ 27231-36-3 ]
  • 6-[(5-methyl-1H-benzimidazol-2-yl)thio]methyl}pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 50
  • [ 110-52-1 ]
  • [ 27231-36-3 ]
  • 9-methyl-2,3,4,5-tetrahydrobenzo[4,5]imidazo[2,1-b][1,3]thiazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 51
  • [ 3043-28-5 ]
  • [ 27231-36-3 ]
  • 3-[(5-methyl-1H-benzimidazol-2-yl)thio]pentane-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 25℃;
  • 52
  • [ 27231-36-3 ]
  • [ 74-88-4 ]
  • [ 91168-31-9 ]
YieldReaction ConditionsOperation in experiment
98.9% With potassium hydroxide In ethanol; water at 5 - 10℃; for 2.5h;
  • 53
  • [ 571957-70-5 ]
  • [ 27231-36-3 ]
  • diethyl 1,4-dihydro-4-(2'-ethoxy-6'-pentadecylphenyl)-6-methyl-2-(2'-mercapto-1'H-benzimidazolyl)methyl-3,5-pyridine dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 20℃; for 2h; 16 [0316] 2-Ethoxy-6-pentadecyl benzaldehyde (3 g, 8.3 mmol) and 4-chloro ethyl acetoacetate (1.36 g, 8.3 mmol) were dissolved in n-butanol (20 mL). Acetic acid (0.5 g, 8.3 mmol) and piperidine (0.7 g, 8.3 mmol) were added and stirred at room temperature for 3-4 hrs. Ethyl-3-amino crotonate (1.08 g, 8.3 mmol) was then added and refluxed for 10 hrs. n-Butanol was evaporated and reaction mixture was washed with distilled water and extracted with dichloromethane (10 mL). Organic layer was dried over sodium sulfate, evaporated and compound was purified by column chromatography using silicagel (100-200 mesh) with hexane:EtOAc (94:6) solvent system to give diethyl 1,4-dihydro-4-(2?-ethoxy-6?-pentadecylphenyl)-6-methyl-2-chloromethyl-3,5-pyridine dicarboxylate. This compound (0.6 g, 1 mmol) was dissolved in dichloromethane (10 mL) and then (5?-methyl) 2-mercapto-1H-bezimidazole (0.164 g, 1 mmol) and NaOH (0.04 g, 1 mmol) were charged. Catalytic amount of tetrabutyl ammonium bromide and dibenzo-18-crown-6 were added and magnetically stirred at room temperature for 2 hrs. The final compound was purified by column chromatography as mentioned in Example 7.
  • 54
  • [ 496-72-0 ]
  • [ 27231-36-3 ]
YieldReaction ConditionsOperation in experiment
With carbon disulfide; sodium hydroxide In hydrogenchloride; ethanol 88 6-[[(5-Methyl-1H-benzimidazol-2-yl)thio]-methyl]-2-pyridinamine hemihydrate EXAMPLE 88 6-[[(5-Methyl-1H-benzimidazol-2-yl)thio]-methyl]-2-pyridinamine hemihydrate A mixture of 12.2 g (0.1 mole) of 3,4-diaminotoluene, 35 ml of carbon disulfide, and 4.0 g (0.1 mole) of sodium hydroxide was heated at reflux in 350 ml of ethanol. After 2.5 hours the mixture was concentrated in vacuo. The residue was suspended in 200 ml of 4% aqueous hydrochloric acid, and the product was collected by filtration, washed sequentially with water and diethyl ether, and air dried to yield 12.2 g of 2-mercapto-5-methylbenzimidazole, as confirmed by the nmr and infrared spectra.
With carbon disulfide; sodium hydroxide In hydrogenchloride; ethanol 12 2-[(imidazo[1,2-a]pyridin-8-ylmethyl)thio]-5-methyl-1H-benzimidazole hemihydrate STR21 EXAMPLE 12 2-[(imidazo[1,2-a]pyridin-8-ylmethyl)thio]-5-methyl-1H-benzimidazole hemihydrate STR21 A mixture of 12.2 g (0.1 mole) of 3,4-diaminotoluene, 35 ml of carbon disulfide, and 4.0 g (0.1 mole) of sodium hydroxide was heated at reflux in 350 ml of ethanol. After 2.5 hours the mixture was concentrated in vacuo. The residue was suspended in 200 ml of 4% aqueous hydrochloric acid, collected by filtration, washed sequentially with water and diethyl ether, and air dried to yield 12.2 g of 2-mercapto-5-methylbenzimidazole, as confirmed by the nmr and infrared spectra.
  • 55
  • [ 2033-76-3 ]
  • [ 27231-36-3 ]
  • [ 340739-82-4 ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate In acetone for 3h; Heating / reflux; 5-Me-D-01c A suspension of 5 -methyl- l//-benzoimidazole-2-thiol (492 mg, 3 mmol), l-(2-bromo-ethoxy)-4-chloro-benzene (777 mg, 3.3 mmol) and K2CO3 (828 mg, 6 mmol) in acetone(10 ml) is refluxed for 3 h. It is cooled down and filtered on filter paper. The solvent isremoved in vacua and the crude purified by flash chromatography on silica-gel (AcOEt/ heptane, 3:7), yielding the title compound (530 mg) in 55% as an off-white solid: fo =2.02 min (LC-2), ESI-MS (pos.): m/z 319.21 [M+H]+, ESI-MS (neg.): m/z 317.23 [M-H]+; JH-NMR (CDC13): 6 (ppm) 2.36 (s, 3H, Me), 3.59 (t, 2H, SCH2), 4.23 (t, 2H,), 6.75 (d, 2Harom), 6.97 (d, 1 Harom), 7.13 (d, 2 Harom), 7.18 (s, 1 Harom), 7.34 (d,
  • 56
  • 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) [ No CAS ]
  • [ 353-83-3 ]
  • [ 27231-36-3 ]
  • [ 105771-14-0 ]
  • [ 105771-15-1 ]
YieldReaction ConditionsOperation in experiment
With 2,6-dichloro-benzonitrile In <i>N</i>-methyl-acetamide 1 5-Methyl-2-(2,2,2-trifluoroethylsulfonyl)-1H-benzimidazole A mixture of 2-mercapto-5-methylbenzimidazole (10 g, 0.061 mole), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (9.1 g, 0.073 mole) and 1-iodo-2,2,2-trifluoroethane (15.4 g, 0.073 mole) in 100 ml dimethylformamide is heated at 45°-5° C. under a nitrogen atmosphere. Over the next five hours additional amounts of 1-iodo-2,2,2-trifluoroethane (12.8 g, 0.061 mole) and DBN (2 g, 0.016 mole) are added. After heating for 9 hours, the reaction mixture is poured into 600 ml ice and water. The precipitated product is collected by filtration, dried and recrystallized from toluene-ligroine giving 5-methyl-2-(2,2,2-trifluoroethylmercapto)-1H-benzimidazole (8.75 g, 0.036 mole), m.p. 159°-161° C. Elemental Analysis for C10 H9 F3 N2 S: Calculated: C, 48.78; H, 3.68; N, 11.38; S, 13.02. Found: C, 49.10; H, 4.07; N, 11.74; S, 12.58.
  • 57
  • [ 30489-43-1 ]
  • [ 27231-36-3 ]
  • 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)thio]-5-methyl-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; acetic acid In hydrogen bromide 5 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)thio]-5-methyl-1H-benzimidazole 1/4 hydrate STR13 Example 5 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)thio]-5-methyl-1H-benzimidazole 1/4 hydrate STR13 A mixture of 903 mg (5.5 mmole) of 2-mercapto-5-methylbenzimidazole and 805 mg (5.4 mmole) of 3-hydroxymethylimidazo[1,2-a]pyridine (prepared as in Example 1) was dissolved in 10 ml of 48% aqueous hydrobromic acid and 10 ml of acetic acid and heated to reflux. After being cooled to room temperature, the mixture was poured into water and made alkaline with potassium carbonate. The oil that separated was extracted into dichloromethane, washed with water, dried over magnesium sulfate, filtered, and concentrated to an oil that crystallized on standing. The solid was collected by filtration, washed with diethyl ether, and air dried to yield the title compound as 610 mg of analytically pure solid. Structure assignment was supported by the nmr and infrared spectra and by elemental analysis. Analysis. Calcd. for C16 H14 N4 S. 1/4H2 O: C, 64.29; H, 4.89; N, 18.78; S, 10.72. Found: C, 64.57; H, 4.77; N, 18.76; S, 10.84.
  • 58
  • [ 27231-36-3 ]
  • [ 107-05-1 ]
  • [ 105770-74-9 ]
YieldReaction ConditionsOperation in experiment
In ethanol 15 5-Methyl-2-(2-propenylthio)-benzimidazole EXAMPLE 15 5-Methyl-2-(2-propenylthio)-benzimidazole 4.11 g (25 mmoles) of 5-methyl-benzimidazoline-2-thione and 2.45 ml of allyl chloride are refluxed in ethanol, then the reaction mixture is evaporated. The residue is worked up according to the method described in Example 2. The residue obtained after the dichloromethane extraction is recrystallized from 7 ml acetonitrile. 3.29 g (64.66 %) of 5-methyl-2-(2-propenyl-thio)benzimidazole melting at a temperature of 128° C. are obtained. Elemental analysis (C11 H12 N2 S) M.: 204.3): Calculated % C, 64.66 H, 5.92 N, 13.72. Found % C, 64.27 H, 5.95 N, 13.91. Spectroscopic data: IR(KBr): ν=3200-2200 (N--H), 1620 (C=C+C=N), 982, 920 (--CH=CH), 1580 (aromatic skeleton), 800 (aromatic H def.) cm-1. NMR (CDCl3 +DMSOd6) δ=2.5 s (Ar--CH3), 3.9 d (S--CH2), ~5.2 m (=CH2), ~6 m (--CH), 6.9-7.5 m (Ar--H), 11.7 bx (N--H) ppm.
  • 59
  • [ 30515-28-7 ]
  • [ 27231-36-3 ]
  • 2-(5-hydroxypentylthio)-5-methylbenzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydroxide; In ethanol; Synthesis of 2-(5-hydroxypentylthio)-5-methylbenzimidazole 2.46 g of 5-methyl-2-mercaptobenzimidazole and 3.4 g of <strong>[30515-28-7]5-bromopentylacetate</strong> were dissolved in 30 ml of ethanol and the mixture was refluxed with stirring under heating for 7 hours. After cooling to room temperature, the reaction mixture was added with was 22.5 ml of 2 N sodium hydroxide solution and stirred at room temperature for 1 hour, and then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol = 95:5) to obtain 3.04 g of the title compound as pale yellow oil (yield: 81%).
  • 60
  • [ 111-24-0 ]
  • [ 27231-36-3 ]
  • 1,5-bis(5-methyl-2-benzimidazoylthio)pentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% 1.5 (5) (5) Synthesis of 1,5-bis(5-methyl-2-benzimidazoylthio)pentane (compound I-1): 8.1 g (yield: 82%) of the intended compound was obtained from 8.2 g of 2-mercapto-5-methylbenzimidazole and 5.5 g of 1,5-dibromopentane in the same manner as in (1). Melting point: 161 to 163° C.; Elementary analysis for C21 H24 N4 S2: Calculated: C 63.60; H 6.10; N 14.13 (%); Found: C 63.42; H 6.02; N 14.29 (%)
  • 61
  • 2-chloromethyl-3,5-dimethyl-4-nitro-pyridine hydrochloride [ No CAS ]
  • [ 56-37-1 ]
  • [ 27231-36-3 ]
  • [ 142885-91-4 ]
YieldReaction ConditionsOperation in experiment
81.1% With sodium hydroxide; In dichloromethane; water; Example 6 5-Methoxy-2-[(3,5-dimethyl-4-nitro-2-pyridinyl)methylthio]-1H-benzimidazole (IX) Method-A To a suspension of 5-methyl-2-mercaptobenzimidazole (36 gm, 0.2 mole), 2-Chloromethyl-3,5-dimethyl-4-nitropyridine hydrochloride (VII) (47.4 gm, 0.2 mole) and triethyl benzylammonium chloride (5 gm) in a dichloromethane (500 ml) was added dropwise a solution of NaOH (17.6 gm, 0.44 mole) in water (30 ml). The addition was exothermic and the temperature was observed to rise to 40 C. with reflux of dichloromethane-the reaction mixture was stirred for further 6 hours at ambient temperature and filtered. The cake was washed with water and dried in vacuum oven to yield 55.8 gm of cream color product. Yield 81.1% gm; Melting Point 124-128 C.; 1H NMR (in CDCl3), 2.34 (s, 3H), 2.38 (s, 3H), 3.83 (s, 3H) 4.51 (s, 2H), 6.86 (dd, J-9 Hz, 13 Hz, 1H), 7.21 (d, J-13 Hz, 1H), 7.57 (d, J-9 Hz, I H), 8.51 (s, 1H), 11.2 (s, exchange with D2O, 1H).
  • 62
  • [ 4701-17-1 ]
  • [ 27231-36-3 ]
  • [ 920536-51-2 ]
YieldReaction ConditionsOperation in experiment
47% With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h; 101 Example 101 Example 101: 4-[5-(5-methyl-1H-benzimidazol-2-ylsulfanyl)-thiophen-2-yl]-2,4,6,7,8,9-hexahydro-pyrazolo[3,4-b]quinolin-5-one Preparation of the aldehyde: a mixture of 0.82 g 2-mercapto-5-methylbenzimidazol (5 mmoles), 0.6 ml of 5-bromo-2-thiophenecarboxaldehyde (5 mmoles) and 1.4 g of potassium carbonate in 10 ml of DMF is heated at 110°C for 2 hours. The mixture is cooled down at room temperature then poured into 200 ml of water and extracted with twice 50 ml of ethyl acetate. The combined organic phases are washed with brine, dried over MgS04 and evaporated. The crude is purified on silica gel using DCM/MeOH as eluent giving 0.65 g of 5-(5-methyl-1H-benzimidazol-2-ylsulfanyl)-thiophene-2-carbaldehyde. (Yield= 47%). ([M+H]+): 275). Ret. Time 3.42 min (gradient 5 to 85% acetonitrile in 7 min).
  • 63
  • [ 72336-24-4 ]
  • [ 27231-36-3 ]
  • [ 1007309-23-0 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In acetone Heating;
  • 64
  • [ 7681-65-4 ]
  • [ 27231-36-3 ]
  • [ 983-81-3 ]
  • [CuI(trans-1,2-bis(diphenylphosphino)ethene)(MeC7H5N2S)]2 [ No CAS ]
  • 65
  • mer,trans-[TcCl3(PPh3)2(MeCN)] [ No CAS ]
  • [ 14842-08-1 ]
  • [ 27231-36-3 ]
  • [AsPh4]([Tc(triphenylphosphine)Cl(5-methyl-1H-benzoimidazole-2-thiol)3]Cl3) [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With PPh3 In methanol; benzene a soln. of 5-methyl-1H-benzimidazole-2-thiol in methanol, PPh3 as a solid and AsPh4Cl in MeOH added to a stirred suspn. of Tc complex in C6H6 kept under N2 stream, refluxed for 30 min; evapd. (vac.), treated with CH2Cl2 and C6H6, washed with hot C6H6 and acetone, dried with Et2O; elem. anal.;
  • 66
  • [ 34387-57-0 ]
  • [ 14842-08-1 ]
  • [ 27231-36-3 ]
  • [AsPh4]([Re(triphenylphosphine)Cl(5-methyl-1H-benzoimidazole-2-thiol)3]Cl3) [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With PPh3 In methanol; benzene a soln. of 5-methyl-1H-benzimidazole-2-thiol in methanol, PPh3 as a solid and AsPh4Cl in MeOH added to a stirred suspn. of Re complex in C6H6 kept under N2 stream, refluxed for 30 min; evapd. (vac.), treated with CH2Cl2 and C6H6, washed with hot C6H6 and acetone, dried with Et2O; elem. anal.;
  • 67
  • [ 27721-02-4 ]
  • silver nitrate [ No CAS ]
  • [ 27231-36-3 ]
  • [silver(I)(μ-1,5-bis(diphenylphosphino)pentane)(5-methyl-benz-1,3-imidazole-2-thione)nitrate]n [ No CAS ]
  • 68
  • [ 27231-36-3 ]
  • [ 946154-93-4 ]
YieldReaction ConditionsOperation in experiment
20% With copper(l) iodide; potassium carbonate; ethylene glycol In N,N-dimethyl acetamide at 200℃; for 0.166667h; microwave irradiation; 8.A To a 5ml Biotage vial equipped with a stir bar was added (12aS,6aR)-9-iodo-4- methoxy-7,7-dimethyl-7,12,12a,6a-tetrah.ydrochromano[4,3-b]quinoline (50 mg), 2- mercapto-5-methylbenzimidazole (20 mg), K2CO3 (32 mg), ethylene glycol (14 μl), CuI (23 mg), and N,N-dimethylacetamide (3 mL). The vial was subjected to irradiation in a chemistry microwave (Emrys Optimizer) for 10 minutes at a temperature of 200°C, then cooled and filtered. After removal of the solvent under reduced pressure the residue was subjected to preparative thin layer chromatography, eluting with ethyl acetate/hexanes (30%). Evaporation of the solvent provided (12aS,6aR)-9-(4-fluorophenyl)-4-methoxy- 7,7-dimethyl-7,12,12a,6a-tetrahydrochromano[4,3-b]quinoline (10.7 mg, 20% yield).1HNMR (400 MHz5 CDCl3): δ 7.41 (d, IH); 7.36-7.30 (m, IH); 7.27 (dd, IH); 7.24-7.19 (m, IH); 7.19 (t, IH); 6.98 (dd, IH); 6.54 (d, IH); 6.51 (d, IH); 6.45 (d, IH); 4.86 (d, IH); 4.60 (s, IH); 4.21 (dd, IH); 3.92 (s, 3H); 3.61 (t, IH); 2.42 (s, 3H); 1.97 (dt, IH); 1.45 (s, 3H); 1.38 (s, 3H).
  • 69
  • [ 19275-82-2 ]
  • [ 27231-36-3 ]
  • [ 1173986-06-5 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In acetone at 20℃;
  • 70
  • [ 598-78-7 ]
  • [ 27231-36-3 ]
  • [ 728035-45-8 ]
YieldReaction ConditionsOperation in experiment
88% With potassium hydroxide In ethanol for 6h; Reflux;
  • 71
  • 3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride [ No CAS ]
  • [ 27231-36-3 ]
  • [ 1182733-62-5 ]
YieldReaction ConditionsOperation in experiment
75% With sodium carbonate for 0.05h; Microwave irradiation;
  • 72
  • [ 3034-48-8 ]
  • [ 27231-36-3 ]
  • [ 209670-34-8 ]
  • 73
  • [ 20098-48-0 ]
  • [ 27231-36-3 ]
  • [ 315228-21-8 ]
  • [ 315228-21-8 ]
YieldReaction ConditionsOperation in experiment
A round-bottomed flask was charged with 2-mercapto-5-methylbenzimidazole (4.84 g, 29.5 mmol), potassium hydroxide (1.66 g, 29.5 mmol), and water (18 mL). This suspension was heated to 120 C. for 3.0 hours. Then <strong>[20098-48-0]3,4,5-trichloronitrobenzen</strong>e (6.68 g, 29.5 mmol) dissolved in 53 mL of n-butanol was added dropwise while the reaction stirred at 120 C. All the white solids went into solution and the solution proceeded to turn a deep red color. The reaction was left stirring for five days, at which point a yellow precipitate was seen. The reaction was then cooled to room temperature and the precipitate was filtered and washed with distilled water to yield 8.10 g (78%) of compound 150 as canary yellow crystals which were a 50/50 mixture of both possible tautomers. 1H NMR (400 MHz) (d6-DMSO) delta 12.64 (1H, s); 8.48 (2H, d, J=2.2 Hz); 7.34 and 7.27 (1H, 2 tautomeric doublets, J=8.3 Hz); 7.26 and 7.19 (1H, 2 tautomeric singlets); 6.99 and 6.95 (1H, 2 tautomeric doublets, J=8.1 Hz); 2.38 and 2.35 (3H, 2 tautomeric singlets).
  • 74
  • [ 62981-82-2 ]
  • [ 27231-36-3 ]
  • [ 1224514-00-4 ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: 2-amino-6-methyl-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidine; 5-methyl-1H-benzoimidazole-2-thiol In ethanol; water at 90℃; for 0.5h; Stage #2: With iodine In ethanol; water at 90℃;
  • 75
  • [ 243668-27-1 ]
  • [ 27231-36-3 ]
  • [ 1250299-17-2 ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine In acetone at 20℃; for 1h;
  • 76
  • [ 27231-36-3 ]
  • [ 56653-43-1 ]
  • [ 1250299-11-6 ]
YieldReaction ConditionsOperation in experiment
78% With triethylamine In acetone at 20℃; for 1h;
  • 77
  • [ 698-63-5 ]
  • [ 27231-36-3 ]
  • [ 842957-71-5 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 5-methyl-1H-benzoimidazole-2-thiol With sodium hydride In tetrahydrofuran for 0.5h; Heating / reflux; Stage #2: 5-nitrofurane-2-carboxaldehyde In tetrahydrofuran for 0.5h; 70 Example 70 Example 70: 4-[5-(5-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-2,4,6,7,8,9-hexahydro-pyrazolo[3,4-b]quinolin-5-one; compound with trifluoro-acetic acid; compound with trifluoro-acetic acid Preparation of the aldehyde: to a solution of 0.82 g of 2-mercapto-5-methyl benzimidazole (5 mmoles) in 10 ml of dry THF is added 200mg of sodium hydride suspension (60% suspension in mineral oil) (5 mmoles). The reaction mixture is refluxed for 1/2 hour. The mixture is cooled to room temperature and 0.71g of 5-nitrofuraldehyde (5 mmoles) in 5 ml of THF is added dropwise. The reaction mixture is stirred during 1/2 hour and then poured into 200 ml of water. The mixture is extracted with twice 75 ml of EtOAc. The combined organic phases are washed with brine, dried over MgS04 and evaporated. The crude is purified on silica gel using DCM/MeOH 97/3 as eluent. 1.07 g of 5-(6-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde is isolated as a black glassy solid (yield=83%). ([M+H]+): 259. Ret. Time: 3.64 min (gradient 0 to 50 % acetonitrile in 7 min).
  • 78
  • [ 698-63-5 ]
  • [ 27231-36-3 ]
  • [ 842957-71-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-methyl-1H-benzoimidazole-2-thiol With sodium hydride In tetrahydrofuran for 0.5h; Heating / reflux; Stage #2: 5-nitrofurane-2-carboxaldehyde In tetrahydrofuran at 20℃; 108.1 5-(5-Methyl-1 H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde 1.16 g of 2-mercapto-5-methylbenzimidazole in 14 mL of tetrahydrofurane (THF) is dropped into a 100 mL three-neck flask, and then 309 mg of sodium hydride is added. The mixture is stirred at reflux temperature during 30 minutes followed by addition of 1 g of 5-nitro furaldehyde in 7 mL of THF. The reaction medium is allowed to cool down to room temperature (ca. 20°C), and then poured in a mixture of 200 mL of water and 100 mL of ethyl acetate (EtOAc). The organic layer is isolated and the aqueous layer is extracted twice with EtOAc (2 x 100 mL). The organic layers are joined together, dried under magnesium sulfate, and evaporated under reduced pressure. 1.8 g of 5-(5-Methyl-1H-benzoimidazol-2-ylsulfanyl)-furan-2-carbaldehyde is collected (RT 2.98 min; [M+H]+ : 259; 80% UV)
  • 79
  • [ 900475-64-1 ]
  • [ 27231-36-3 ]
  • [ 1261579-42-3 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 5-methyl-1H-benzoimidazole-2-thiol With sodium hydroxide In ethanol for 1h; Reflux; Stage #2: ethyl 2-(2-chloroethyl)-3,4-dihydro-5-methyl-4-oxothieno[2,3-d]pyrimidin 6-carboxylate In ethanol Reflux;
  • 80
  • [ 70-11-1 ]
  • [ 27231-36-3 ]
  • [ 141075-26-5 ]
YieldReaction ConditionsOperation in experiment
83% In acetone at 20℃; for 1h;
  • 81
  • [ 27231-36-3 ]
  • [ 74-88-4 ]
  • [ 637322-92-0 ]
YieldReaction ConditionsOperation in experiment
89% With N-ethyl-N,N-diisopropylamine In acetone at 20℃; for 0.0833333h; Sonication;
  • 82
  • [ 19614-12-1 ]
  • [ 27231-36-3 ]
  • [ 1353998-94-3 ]
  • [ 1353998-95-4 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; caesium carbonate; <i>L</i>-proline In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere; (A) Typical Experimental Procedure Experimental Procedure for Copper-Catalyzed One-Pot Synthesis of benzimidazobenzothiazine (3a) (Table 2, entry 1). General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, 2-mercaptobenzimidazole 1a (125 mg, 0.5 mmol), isothiocyanatobenzene 2a (75 mg, 0.5 mmol), Cs2CO3 (652 mg, 2.0 mmol), CuI (10 mg, 0.05 mmol, 10 mol %), L-Proline (16.5 mg, 0.10 mmol, 20 mol %). The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, DMF (2.0 mL) was added by syringe and the mixture was pre-stirred for several minutes. The tube was sealed and the mixture was allowed to stir at 110 °C for 20 h. The reaction was stopped and cooled to room temperature. Then the cooled reaction mixture was dissolved in H2O and extracted with Et2O. The combined organic layer was dried (MgSO4), then concentrated by rotatory evaporation. The crude residue was purified by column chromatography on silica gel using petroleum/ethyl acetate as eluent to give a yellow solid of benzimidazobenzothiazine (3a) (97.7 mg, 82%).
  • 83
  • [ 66192-24-3 ]
  • [ 27231-36-3 ]
  • [ 1353998-97-6 ]
  • [ 1353998-98-7 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; caesium carbonate; <i>L</i>-proline In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere; (A) Typical Experimental Procedure Experimental Procedure for Copper-Catalyzed One-Pot Synthesis of benzimidazobenzothiazine (3a) (Table 2, entry 1). General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, 2-mercaptobenzimidazole 1a (125 mg, 0.5 mmol), isothiocyanatobenzene 2a (75 mg, 0.5 mmol), Cs2CO3 (652 mg, 2.0 mmol), CuI (10 mg, 0.05 mmol, 10 mol %), L-Proline (16.5 mg, 0.10 mmol, 20 mol %). The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, DMF (2.0 mL) was added by syringe and the mixture was pre-stirred for several minutes. The tube was sealed and the mixture was allowed to stir at 110 °C for 20 h. The reaction was stopped and cooled to room temperature. Then the cooled reaction mixture was dissolved in H2O and extracted with Et2O. The combined organic layer was dried (MgSO4), then concentrated by rotatory evaporation. The crude residue was purified by column chromatography on silica gel using petroleum/ethyl acetate as eluent to give a yellow solid of benzimidazobenzothiazine (3a) (97.7 mg, 82%).
  • 84
  • [ 27231-36-3 ]
  • [ 3433-80-5 ]
  • [ 1353998-93-2 ]
  • [ 1353998-92-1 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; caesium carbonate; <i>L</i>-proline In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere; (A) Typical Experimental Procedure Experimental Procedure for Copper-Catalyzed One-Pot Synthesis of benzimidazobenzothiazine (3a) (Table 2, entry 1). General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, 2-mercaptobenzimidazole 1a (125 mg, 0.5 mmol), isothiocyanatobenzene 2a (75 mg, 0.5 mmol), Cs2CO3 (652 mg, 2.0 mmol), CuI (10 mg, 0.05 mmol, 10 mol %), L-Proline (16.5 mg, 0.10 mmol, 20 mol %). The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, DMF (2.0 mL) was added by syringe and the mixture was pre-stirred for several minutes. The tube was sealed and the mixture was allowed to stir at 110 °C for 20 h. The reaction was stopped and cooled to room temperature. Then the cooled reaction mixture was dissolved in H2O and extracted with Et2O. The combined organic layer was dried (MgSO4), then concentrated by rotatory evaporation. The crude residue was purified by column chromatography on silica gel using petroleum/ethyl acetate as eluent to give a yellow solid of benzimidazobenzothiazine (3a) (97.7 mg, 82%).
  • 85
  • [ 27231-36-3 ]
  • 5-methyl-2-(2-pyridylmethylsulfanyl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.7% With sodium hydroxide In methanol; water at 70℃; for 12h;
  • 86
  • [ 27231-36-3 ]
  • [ 99860-36-3 ]
  • [ 1269527-18-5 ]
YieldReaction ConditionsOperation in experiment
58% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;
  • 87
  • [ 27231-36-3 ]
  • [ 99860-38-5 ]
  • [ 1269527-20-9 ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;
  • 88
  • [ 1453858-89-3 ]
  • [ 27231-36-3 ]
  • [ 1453858-91-7 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydroxide In methanol at 20℃; for 6h; General Procedure for the Preparation of 4 (a-e) General procedure: To a solution of 5-substituted mercaptobenzimidazole (13.3 mmol), methanol(50.0 mL) NaOH (29.7 mmol) was added compound 3 (5 gm, 11.97 mmol) and the reactionmixture was stirred for 6 h at r.t. and monitored the reaction by TLC. Upon completion ofthe reaction, methanol was removed under reduced pressure and the resulting product wasdissolved in water (50 mL) and the pH was adjusted to 6.0-7.0 with HCl. The product wasextracted into DCM. The organic layer was separated and washed with water followed by20% sodium chloride solution and dried over anhydrous Na2SO4. The solvent was distilledoff under vacuum to obtain crude product 4a-e. The crude product was recrystallized fromethylacetate to obtain the pure title compounds.
  • 89
  • [ 67-56-1 ]
  • [ 603-35-0 ]
  • [ 7787-70-4 ]
  • [ 27231-36-3 ]
  • [CuBr(2-mercapto-5-methylbenzimidazole)(triphenylphosphine)2]*2CH3OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% In dichloromethane Synthesis of complexes 1-7 General procedure: Compound 1: A mixture of CuCl (0.0198 g, 0.2 mmol) and HMNBT (0.0424 g, 0.2 mmol, HMNBT = 2-mercapto-6-nitrobenzothiazole) in MeOH and CH2Cl2 (10 mL, v/v = 1:1) was stirred for 2 h and PPh3 (0.1049 g, 0.4 mmol) was added to the mixture which was stirred for further 4 h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature for a week to yield orange crystalline products. Compounds 2-3 was prepared in a manner similar to that described for 1, using CuCl (0.0198 g, 0.2 mmol) or CuBr (0.0287 g, 0.2 mmol), HMNBT (0.0424 g, 0.2 mmol) and PPh3 (0.0525 g, 0.2 mmol) as starting materials. After three days, orange crystals were formed. Compound 4: using CuSCN (0.0243 g, 0.2 mmol), HMNBT (0.0424 g, 0.2 mmol), PPh3 (0.0525 g, 0.2 mmol) as starting materials.Afterthree days, orange crystals were formed. Compound 5: using CuBr(0.0287 g, 0.2 mmol), HAMTD (0.0266 g, 0.2 mmol, HAMTD = 2-amino-5-mercapto-1,3,4-thiadiazole), PPh3 (0.1049 g, 0.4 mmol)as starting materials. After a week, colorless crystals were formed.Compounds 6-7: using CuBr (0.0287 g, 0.2 mmol) or CuI (0.0381 g,0.2 mmol), MMBD (0.0328 g, 0.2 mmol, MMBD = 2-mercapto-5-methyl-benzimidazole), PPh3 (0.1049 g, 0.4 mmol) as startingmaterials. After a week, colorless crystals were formed
  • 90
  • [ 67-56-1 ]
  • [ 7681-65-4 ]
  • [ 603-35-0 ]
  • [ 27231-36-3 ]
  • [CuI(2-mercapto-5-methylbenzimidazole)(triphenylphosphine)2]*2CH3OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% In dichloromethane Synthesis of complexes 1-7 General procedure: Compound 1: A mixture of CuCl (0.0198 g, 0.2 mmol) and HMNBT (0.0424 g, 0.2 mmol, HMNBT = 2-mercapto-6-nitrobenzothiazole) in MeOH and CH2Cl2 (10 mL, v/v = 1:1) was stirred for 2 h and PPh3 (0.1049 g, 0.4 mmol) was added to the mixture which was stirred for further 4 h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature for a week to yield orange crystalline products. Compounds 2-3 was prepared in a manner similar to that described for 1, using CuCl (0.0198 g, 0.2 mmol) or CuBr (0.0287 g, 0.2 mmol), HMNBT (0.0424 g, 0.2 mmol) and PPh3 (0.0525 g, 0.2 mmol) as starting materials. After three days, orange crystals were formed. Compound 4: using CuSCN (0.0243 g, 0.2 mmol), HMNBT (0.0424 g, 0.2 mmol), PPh3 (0.0525 g, 0.2 mmol) as starting materials.Afterthree days, orange crystals were formed. Compound 5: using CuBr(0.0287 g, 0.2 mmol), HAMTD (0.0266 g, 0.2 mmol, HAMTD = 2-amino-5-mercapto-1,3,4-thiadiazole), PPh3 (0.1049 g, 0.4 mmol)as starting materials. After a week, colorless crystals were formed.Compounds 6-7: using CuBr (0.0287 g, 0.2 mmol) or CuI (0.0381 g,0.2 mmol), MMBD (0.0328 g, 0.2 mmol, MMBD = 2-mercapto-5-methyl-benzimidazole), PPh3 (0.1049 g, 0.4 mmol) as startingmaterials. After a week, colorless crystals were formed
  • 91
  • 2-chloro-N-[4-(2-methyl-4-thiazolyl)phenyl]acetamide [ No CAS ]
  • [ 27231-36-3 ]
  • [ 1581289-53-3 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In acetone for 2h; Reflux;
  • 92
  • [ 583-55-1 ]
  • [ 27231-36-3 ]
  • [ 1611489-29-2 ]
  • [ 1611489-30-5 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; Schlenk technique; Overall yield = 68 %; General procedure for Cu-catalyzed one-pot synthesis of benzimidazo[2,1-b]benzothiazoles General procedure: An oven-dried Schlenk tube was charged with a magneticstir bar, binucleophile 2-mercaptobenzimidazole 2 (1.0 mmol, 1.0 equiv), CuI(0.1 mmol, 10 mol %), phen (0.2 mmol, 20 mol %), and K2CO3 (2.0 mmol, 2equiv). The tube was capped and then evacuated and backfilled with nitrogen(3 times). Under a positive pressure of nitrogen, a solution of o-dihaloarene 1(1.05 mmol, 1.05 equiv) in DMF (3 mL) was added via syringe. The tube wassealed and allowed to stir at 120 C (monitored by TLC). After being cooled toroom temperature, EtOAc (40 mL) was added and the mixture was washedwith brine (20 mL 3). The organic phase was dried over Na2SO4 andconcentrated. The residue was purified by column chromatography on silicagel using petrol/EtOAc (10:1?3:1, v:v) as eluent to give product 3.
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