[ CAS No. 583-39-1 ] {[proInfo.proName]}

Name: 583-39-1|1,3-Dihydro-2H-benzo[d]imidazole-2-thione|97%
Brand: Ambeed
SKU: A523734
Price: 5.0 USD
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Quality Control of [ 583-39-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 583-39-1 ]

SDS Specification

Alternatived Products of [ 583-39-1 ]

Product Details of [ 583-39-1 ]

CAS No. :	583-39-1	MDL No. :	MFCD00466107
Formula :	C₇H₆N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YHMYGUUIMTVXNW-UHFFFAOYSA-N
M.W :	150.20	Pubchem ID :	707035
Synonyms :		Chemical Name :	1,3-Dihydro-2H-benzo[d]imidazole-2-thione

Calculated chemistry of [ 583-39-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.35
TPSA :	67.48 Å²

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) :	-5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.26
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	1.85
Log Po/w (MLOGP) :	1.25
Log Po/w (SILICOS-IT) :	2.35
Consensus Log Po/w :	1.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.53
Solubility :	0.44 mg/ml ; 0.00293 mol/l
Class :	Soluble
Log S (Ali) :	-2.77
Solubility :	0.253 mg/ml ; 0.00168 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.0
Solubility :	0.15 mg/ml ; 0.000995 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.02

Safety of [ 583-39-1 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P260-P264-P270-P272-P273-P280-P301+P310+P330-P302+P352-P314-P333+P313-P405-P501	UN#:	2811
Hazard Statements:	H301-H317-H373-H412	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 583-39-1 ]

* 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.

Upstream synthesis route of [ 583-39-1 ]
Downstream synthetic route of [ 583-39-1 ]

[ 583-39-1 ] Synthesis Path-Upstream 1~3

1
[ 583-39-1 ]
[ 4857-06-1 ]

Reference： [1] Synthetic Communications, 1998, vol. 28, # 9, p. 1703 - 1712

2
[ 2253-73-8 ]
[ 95-54-5 ]
[ 583-39-1 ]
[ 2986-17-6 ]

Reference： [1] Chemistry - A European Journal, 2010, vol. 16, # 35, p. 10818 - 10831

3
[ 583-39-1 ]
[ 54624-57-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 5, p. 1918 - 1924

[ 583-39-1 ] Synthesis Path-Downstream 1~88

1
[ 186581-53-3 ]
[ 583-39-1 ]
[ 60-29-7 ]
[ 555-31-7 ]
[ 7152-24-1 ]
[ 4344-61-0 ]
[ 3418-46-0 ]

Reference： [1]Chemische Berichte,1957,vol. 90,p. 2852,2854

2
[ 186581-53-3 ]
[ 583-39-1 ]
[ 7152-24-1 ]

Reference： [1]Chemische Berichte,1957,vol. 90,p. 2852,2854

3
[ 583-39-1 ]
[ 100-44-7 ]
[ 51290-77-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In acetone; for 3h;Reflux;	General procedure: Benzyl chloride or 1-iodopropane, 89.25 mmol, and potassium carbonate, 170.0 mmol, were added to a solution of 85.0 mmol of 1,3-dihydro-2H-benzimidazole-2-thione in 140 mL of acetone. The mixture was refluxed for 3 h with stirring and poured into water with stirring to dissolve inorganic com-ponents. The precipitate was filtered off and washed with water and methanol. Compound 1b was dried and recrystallized from 20 mL of methanol. Compound 1a required no additional purification. Compound 1a. Yield 93%, colorless crystals, mp 180-181C. 1 H NMR spectrum, delta, ppm: 4.56 s (2H, CH 2 ), 7.07 t (2H, H arom , J = 4.0 Hz), 7.21 t (1H, H arom , J = 6.8 Hz), 7.28 t (2H, H arom , J = 7.2 Hz), 7.35-7.45 m (4H, H arom ), 12.04 br.s (1H, NH). Compound 1b. Yield 55%, colorless crystals, mp 151-152C. 1 H NMR spectrum, delta, ppm: 1.07 t (3H, CH 3 , J = 7.2 Hz), 1.80 sext (2H, CH 2 , J = 6.8 Hz), 3.25 t (2H, CH 2 , J = 7.2 Hz), 7.05 s (2H, H arom ), 7.37 s (1H, H arom ), 12.27 s (1H, NH).

Reference： [1]Russian Journal of Organic Chemistry,2018,vol. 54,p. 1363 - 1368
Zh. Org. Khim.,2018,vol. 54,p. 1350 - 1354,5
[2]Chemija,1959,vol. 2,p. 333,336
Chem.Abstr.,1960,p. 509

4
[ 583-39-1 ]
[ 105-39-5 ]
[ 5429-62-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In isopropyl alcohol; for 5h;Reflux;	Sodium hydroxide (1.6 g, 40 mmol) was dissolved in 2-PrOH (40 ml); benzimidazole-2-thione 1 (6.0 g, 40 mmol) was added followed by ethyl chloroacetate (4.3 ml, 4.9 g, 40 mmol). The reaction mixture was refluxed for 5 h, cooled, and poured into water. The precipitate formed was filtered off, washed with water, dried, and recrystallized from CCl4. Yield 7.2 g (76%), colorless crystals

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1958,vol. 78,p. 1378,1381
Chem.Abstr.,1959,p. 8124
[2]Chemistry of Heterocyclic Compounds,2015,vol. 50,p. 1547 - 1558

5
[ 583-39-1 ]
[ 97-00-7 ]
[ 19919-16-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In ethanol; water; for 3h;Reflux;	General procedure: 2,4-Dinitrochlorobenzene (1 mmol), 2-mercapto-5-substituted benzimidazoles (1 mmol) and Potassium hydroxide (1 mmol) were suspended in aqueous-EtOH (1:1). The reaction mixture was stirred vigorously for about 30 minutes and then refluxed on water bath for 2.5 h, at which point it cleared and TLC analysis indicated complete consumption of the reactants. The reaction mixture was diluted with 50 mL of water and cooled in ice, and the precipitate was collected by filtration. After being washed with cold water (2 x 25 mL), the precipitate was dried under vacuum to afford a pure product (3a-d).

Reference： [1]Annali di Chimica,1955,vol. 45,p. 162,164
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1306 - 1309

6
[ 583-39-1 ]
[ 77-78-1 ]
[ 7152-24-1 ]

Reference： [1]Patent: DE814151,1949,
DRP/DRBP Org.Chem.,

7
[ 583-39-1 ]
[ 79-07-2 ]
[ 30065-26-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium hydroxide; In isopropyl alcohol; for 3h;Reflux;	Sodium hydroxide (1.60 g, 40 mmol) was dissolved in 2-PrOH (70 ml), benzimidazole-2-thione 1 (6.00 g, 40 mmol) was added followed by portionwise addition of chloroacetamide (3.75 g, 40 mmol). The reaction mixture was refluxed for 3 h, cooled, the precipitate was filtered off, washed with water, and dried. Yield 6.75 g (81%), colorless crystals

Reference： [1]Chemistry of Heterocyclic Compounds,2015,vol. 50,p. 1547 - 1558
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1958,vol. 78,p. 1378,1381
Chem.Abstr.,1959,p. 8124

8
[ 583-39-1 ]
[ 74-88-4 ]
[ 7152-24-1 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 11515 - 11530
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1954,vol. 74,p. 1365,1367, 1368
Chem.Abstr.,1955,p. 15876
[3]Journal of the Chemical Society,1949,p. 3311,3314
[4]Phosphorus and Sulfur and the Related Elements,1984,vol. 20,p. 231 - 240
[5]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1573 - 1576

9
[ 583-39-1 ]
[ 5435-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine; acetic acid Anschliessend Behandeln mit NH₃;
	With chlorine; iron(III) chloride Anschliessend Behandeln mit NH₃;

Reference： [1]Roblin; Clapp [Journal of the American Chemical Society, 1950, vol. 72, p. 4890] Pala [Farmaco, Edizione Scientifica, 1958, vol. 13, p. 461,467]
[2]Roblin; Clapp [Journal of the American Chemical Society, 1950, vol. 72, p. 4890] Pala [Farmaco, Edizione Scientifica, 1958, vol. 13, p. 461,467]

10
[ 583-39-1 ]
[ 40828-54-4 ]

Reference： [1]ACS Combinatorial Science,2019,vol. 21,p. 805 - 816
[2]Synthetic Communications,1998,vol. 28,p. 1703 - 1712
[3]Journal of the Chemical Society,1930,p. 2402,2407
[4]Archiv der Pharmazie,1958,vol. 291,p. 180,182

11
[ 75-15-0 ]
[ 95-54-5 ]
[ 583-39-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	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;Catalytic behavior;	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.
75%	With choline chloride?urea; In water; at 100℃; for 4h;Cooling with ice; Green chemistry;	General procedure: In a 10mL round-bottom flask (equipped with a basic gas trap to neutralize exhausted hydrogen sulfide), 2 mmol amine was added to 3 mL distilled water and 0.1 mmol of DES (ChCl-urea). The flask was placed in an ice bath over the magnetic heater-stirrer and the mixture was stirred vigorously. Then, 1 mmol carbon disulfide was added to the mixture during the stirring. The reaction was monitored by TLC, with ethyl acetate-hexane (3:7) mixture as eluent, up to the completion of the reactant. The ice bath was then removed and replaced with an oil bath, the flask was equipped with a condenser and the reaction was heated to 100C and stirred for 3 h with refluxing. Then, the heating was stopped and the reaction was allowed to reach to room temperature. The precipitated product (during the cooling), was purified by recrystallization in ethanol and used for the next analyses. All products are known compounds and their structures were confirmed by comparison of their mass specta, IR, 1H-NMR and 13C-NMR spectra, and melting points with the reported values in the literature [26-30]. The selected physical properties, GC-Mass results and spectroscopic data for all products are listed in section 2.4 and all original spectral data (IR, NMR and mass spectrometry) are shown in the supplementary information.
	With potassium hydroxide; In ethanol; water;	The benzimidazole conjugates have been synthesised according to the following general procedures exemplified with some specific benzimidazole-coumarin conjugates. These procedures can however be applied by a person skilled in the art to other compounds of the invention.For the synthesis of the new benzimidazoles, like 4a-k and the corresponding glucopyranosides, like 7a-h, various substituted phenylenediamines la-f were treated with carbon disulfide (Klimesova, V. et al. J. Eur. J. Med. Chem. 2002, 37, 409-418) and ethanolic KOH in H2O (see Scheme 1). Then NH4OH and 3-chloromethylcoumarins 3a-c were added in sequence to afford the desired benzimidazole-SCH2-coumraines 4a-k. The overall yields were around 53-86%.

Reference： [1]Russian Journal of Organic Chemistry,2006,vol. 42,p. 448 - 450
[2]Organic Preparations and Procedures International,2019,vol. 51,p. 175 - 181
[3]Journal of Sulfur Chemistry,2012,vol. 33,p. 653 - 659
[4]RSC Advances,2019,vol. 9,p. 26768 - 26772
[5]Journal of Chemical Research - Part S,1996,p. 94 - 95
[6]Science China Chemistry,2014,vol. 57,p. 1117 - 1125
[7]ChemMedChem,2013,vol. 8,p. 994 - 1001
[8]Journal of Sulfur Chemistry,2019,vol. 40,p. 113 - 123
[9]Synthesis,2008,p. 3579 - 3584
[10]Gazzetta Chimica Italiana,1893,vol. 23 I,p. 295
[11]Organic Syntheses,1950,vol. 30,p. 56
[12]Canadian Journal of Chemistry,1984,vol. 62,p. 808 - 813
[13]Medicinal Chemistry Research,2012,vol. 21,p. 703 - 710
[14]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1306 - 1309
[15]Patent: WO2007/128086,2007,A2 .Location in patent: Page/Page column 15-16

12
[ 583-39-1 ]
[ 3400-55-3 ]
[ 16458-72-3 ]

Reference： [1]Canadian Journal of Chemistry,1967,vol. 45,p. 2903 - 2912

13
[ 67-56-1 ]
[ 583-39-1 ]
[ 7152-24-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1984,vol. 20,p. 656 - 658
Khimiya Geterotsiklicheskikh Soedinenii,1984,vol. 20,p. 805 - 807
[2]Journal of Organic Chemistry USSR (English Translation),1984,p. 1854
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 2031 - 2032

14
[ 583-39-1 ]
[ 50-00-0 ]
[ 29608-05-7 ]
[ 108176-92-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 877 - 879

15
[ 583-39-1 ]
[ 50-00-0 ]
[ 51013-67-3 ]
[ 108176-81-4 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 877 - 879

16
[ 583-39-1 ]
[ 29086-41-7 ]
[ 84375-36-0 ]

Reference： [1]Monatshefte fur Chemie,1982,vol. 113,p. 1139 - 1144

17
[ 583-39-1 ]
[ 106-93-4 ]
[ 21224-34-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 393 - 395
[2]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 813 - 814

18
[ 583-39-1 ]
[ 109-64-8 ]
[ 34117-49-2 ]

Yield	Reaction Conditions	Operation in experiment
83%		A mixture of 1H-benzo[d]imidazole-2(3H)-thione 1 (0.026 mole, 5 gm) in 60 mL ethanol and inpresence of triethylamine (0.01 mol, 1.39 mL) was refluxed for 1 h, then 1,3-dibromopropane (0.013 mol,2.6 g) was added. The reaction mixture was further heated under reflux for 5 h. Then, ethanol wasremoved under vacuum, and water (20 mL) was added to the product, and kept for 24 h at roomtemperature to give white crystals. The product (4.68 g, 83% yield), was recrystallized from ethanol,TLC, Rf = 0.382 (1:1, n-hexane:ethyl acetate), m.p. 201-202 C. 1H-NMR (DMSO-d6) : 2.29 (m, 2H,CH2), 3.26 (t, 2H, CH2), 4.17 (t, 2H, CH2), 7.11 (m, 2H, Ar-H), and 7.39 ppm (m, 2H, Ar-H). 13C-NMR(DMSO-d6) : 21.9 (CH2), 24.3 (CH2), 41.7 (CH2), 107.9 (CH), 116.1 (CH), 120.02 (CH), 120.94 (CH),134.69 (C), 134.81 (C), 141.4; 145.75 ppm (C=N). Calc. for C10H10N2S (190.26): C, 63.13; H, 5.30;N, 14.72%. Found: C, 63.42; H, 5.11; N, 14.41%.

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 747 - 751
[2]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 393 - 395
[3]Molecules,2016,vol. 21

19
[ 583-39-1 ]
[ 91-13-4 ]
2,5-dihydro(6H)7,8-diphenylbenzimidazo<2,1-b>-1,3-benzothiazepine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 393 - 395

20
[ 583-39-1 ]
[ 51-17-2 ]
[ 40828-54-4 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1984,p. 1064 - 1065
[2]Journal of the Chemical Society. Chemical communications,1984,p. 1064 - 1065
[3]Acta Chemica Scandinavica,1995,vol. 49,p. 225 - 229

21
[ 40828-54-4 ]
[ 51-17-2 ]
[ 583-39-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1984,vol. 20,p. 224
Khimiya Geterotsiklicheskikh Soedinenii,1984,vol. 20,p. 266 - 267
[2]Chemistry of Heterocyclic Compounds,1984,vol. 20,p. 224
Khimiya Geterotsiklicheskikh Soedinenii,1984,vol. 20,p. 266 - 267

22
[ 583-39-1 ]
[ 51-17-2 ]

Reference： [1]Acta Chemica Scandinavica,1995,vol. 49,p. 225 - 229
[2]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 2520 - 2524
[3]European Journal of Organic Chemistry,2020

23
[ 583-39-1 ]
[ 96-11-7 ]
[ 5268-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1.) DMSO, reflux, 0.5, 2.) THF, dioxane, 60-80 deg C, 3 h; Yield given. Multistep reaction;

Reference： [1]Popov, I. I. [Chemistry of Heterocyclic Compounds, 1995, vol. 31, # 4, p. 500 - 503][Khimiya Geterotsiklicheskikh Soedinenii, 1995, # 4, p. 567 - 570]

24
[ 583-39-1 ]
[ 96-11-7 ]
1,3-bis(2-benzimidazolylthio)-2-bromopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dimethyl sulfoxide for 3h;

Reference： [1]Popov, I. I. [Chemistry of Heterocyclic Compounds, 1995, vol. 31, # 4, p. 500 - 503][Khimiya Geterotsiklicheskikh Soedinenii, 1995, # 4, p. 567 - 570]

25
[ 103-72-0 ]
[ 95-54-5 ]
[ 583-39-1 ]

Reference： [1]Journal of Chemical Research - Part S,1996,p. 94 - 95
[2]Science China Chemistry,2014,vol. 57,p. 1117 - 1125

26
[ 17356-08-0 ]
[ 95-54-5 ]
[ 583-39-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	In neat (no solvent); for 1h;Milling; Green chemistry;	General procedure: A mixture of 1,2-phenylenediamine (2.5 g, 23.1 mmol) and 25.0 mmol of ammonium thiocyanate,urea or thiourea was introduced into stainless steel vials with appropriate weight of stainless steelballs for the mentioned time. The reaction was poured into water. The formed precipitate was filtered,washed with water and recrystalized from ethanol.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 84
[2]Journal of Chemical Research - Part S,1996,p. 94 - 95
[3]Synthetic Communications,2002,vol. 32,p. 3703 - 3709
[4]Molecules,2016,vol. 21
[5]Heterocyclic Communications,2006,vol. 12,p. 273 - 274
[6]Synthetic Communications,2000,vol. 30,p. 2191 - 2196

27
[ 583-39-1 ]
[ 77-78-1 ]
aqueous NaOH [ No CAS ]
[ 7152-24-1 ]
[ 4344-61-0 ]

Reference： [1]Chemische Berichte,1957,vol. 90,p. 2852,2854

28
[ 110-89-4 ]
[ 583-39-1 ]
[ 7722-84-1 ]
[ 40828-54-4 ]

Reference： [1]Archiv der Pharmazie,1958,vol. 291,p. 180,182

29
[ 56-23-5 ]
[ 583-39-1 ]
[ 7722-84-1 ]
[ 40828-54-4 ]

Reference： [1]Archiv der Pharmazie,1958,vol. 291,p. 180,182

30
[ 583-39-1 ]
[ 7722-84-1 ]
[ 64-19-7 ]
[ 40828-54-4 ]

Reference： [1]Archiv der Pharmazie,1958,vol. 291,p. 180,182

31
[ 583-39-1 ]
[ 7722-84-1 ]
[ 109-89-7 ]
[ 40828-54-4 ]

Reference： [1]Archiv der Pharmazie,1958,vol. 291,p. 180,182

32
[ 583-39-1 ]
[ 7722-84-1 ]
[ 109-73-9 ]
[ 40828-54-4 ]

Reference： [1]Archiv der Pharmazie,1958,vol. 291,p. 180,182

33
[ 110-91-8 ]
[ 583-39-1 ]
[ 50-00-0 ]
[ 6268-88-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	In water; isopropyl alcohol; for 3h;Reflux;	Benzimid-azole-2-thione 1 (1.50 g, 10 mmol) and morpholine (0.87 ml, 0.87 g, 10 mmol) were dissolved in 2-PrOH (30 ml); 37% aqueous formaldehyde (0.90 ml, 12 mmol) was added, and the mixture was refluxed for 3 h (precipitate formed almost immediately). The precipitate was filtered off, dried, and recrystallized from EtOH. The major component of the obtained mixture was compound 3, which partially disproportionated in solution to bis-adduct 2 and the starting compound 1. Yield 1.70 g (68%)

Reference： [1]Russian Journal of General Chemistry,2013,vol. 83,p. 1098 - 1102
Zh. Obshch. Khim.,2013,vol. 83,p. 967 - 971,5
[2]Journal of Chemical Research - Part S,2000,p. 269 - 271
[3]Chemistry of Heterocyclic Compounds,2015,vol. 50,p. 1547 - 1558

34
[ 583-39-1 ]
[ 51-80-9 ]
[ 100531-96-2 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 630 - 632

35
[ 583-39-1 ]
[ 16750-07-5 ]
[ 956475-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 80℃;	Finally, we attached a pyranose moiety onto 2-thiones 2a,b as shown in Scheme 8. Reaction of 2a,b with O-peracety-2-deoxy-beta-D-glucose (20) in the presence of Me3SiOTf generated intermediates 21a,b. The thione moiety therein allowed these compounds to couple with coumarins 3 to produce the desired targets 22a-c in 54-92% yields. Our identification of the structures is exemplified by use of 22b to stand for the target molecules. The mass spectrum of 22b in the positive ion mode under electrospray ionization method exhibited a peak at 611.30 for the species [M + H]+, which indicates the molecular formula to be C3OH3ON2O10S. The three moieties joined together included benzimidazole, coumarin, and1 "i dexoyglucopyranose. The - N=C(-N)(-S) carbon resonated at the 149.35 ppm in the C NMR spectrum. On the other hand, the glycosidic proton resonated at the 5.75 ppm and the two diastereotopic SCH2 protons appeared at 4.58 and 4.49 ppm as two doublets with J= 13.6 Hz in its 1H NMR spectrum.

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1486 - 1490
[2]Patent: WO2007/128086,2007,A2 .Location in patent: Page/Page column 20-21; 41

36
[ 583-39-1 ]
[ 98-80-6 ]
[ 716-79-0 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 4440 - 4448
[2]Advanced Synthesis and Catalysis,2007,vol. 349,p. 448 - 452

37
[ 583-39-1 ]
[ 100872-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: acetic acid; aqueous KMnO₄

Reference： [1]Bednjagina; Postowskii [Chemija, 1959, vol. 2, p. 333,336][Chem.Abstr., 1960, p. 509]

38
[ 583-39-1 ]
[ 69469-81-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrahydrofuran / Ambient temperature 2: methanol / 17 h / Heating 3: aq. NaOH / 5 h / 70 °C
	Multi-step reaction with 2 steps 1: NaOMe / methanol 2: aq. NaOH / 5 h / 70 °C

Reference： [1]Wade,J.J. [Journal of Organic Chemistry, 1979, vol. 44, # 11, p. 1816 - 1819]
[2]Wade,J.J. [Journal of Organic Chemistry, 1979, vol. 44, # 11, p. 1816 - 1819]

39
[ 583-39-1 ]
[ 105-36-2 ]
[ 5429-62-9 ]

Yield	Reaction Conditions	Operation in experiment
77%		A mixture of 1H-benzo[d]imidazole-2(3H)-thione 1 (0.01 mol, 1.5 g), in dry acetone 25 mL andpotassium carbonate (0.01 mol, 1.62 g) was stirred and heated under reflux for 1 h. Ethyl bromoacetate(0.01 mol, 1.67 g, 1.1 mL) was added to the reaction mixture and continuing stirring and heating foranother 15 h until completion of the reaction. The reaction mixture was cooled then filtered off. Waterwas added to the filtrate and left at room temperature for 24 h. The precipitate was filtered off andwashed with water to give product, yield 77%. It was recrystallized from ethanol to give white crystal,m.p. 97-98 C (Lit. [18] m.p. 60-62 C, Lit. [15] m.p. 117 C), TLC, Rf = 0.554 (1:1, n-hexane:ethylacetate) IR (KBr) nu 3457 (NH), 1507 (NH) IP, 1739 (C=O), 1269, 1167 (C-O), 3150 (CH aromatic), and1591 cm-1 (C=C). 1H-NMR (DMSO-d6) delta: 1.13 (t, 3H, CH3), 4.09 (q, 2H, CH2), 4.18 (s, 2H, CH2), 7.1(s, 2H, Ar-H), and 7.40 (d, 2H, Ar-H), 12.60 ppm (s, 1H, NH). 13C-NMR (DMSO-d6) delta: 13.2 (CH3),32.0 (CH2), 60.4 (CH2), 120.7 (Ar-C), 148.3 (C=N), and 167.8 ppm (C=O).

Reference： [1]Molecules,2016,vol. 21

40
[ 583-39-1 ]
[ 2506-41-4 ]
2-[(naphthalen-2'-yl)methylthio]-1H-benzimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1486 - 1490

41
[ 583-39-1 ]
[ 54624-57-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1918 - 1924

42
[ 2253-73-8 ]
[ 95-54-5 ]
[ 583-39-1 ]
[ 2986-17-6 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 10818 - 10831

43
[ 583-39-1 ]
[ 59814-17-4 ]
[ 1254758-61-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7357 - 7364

44
[ 106-31-0 ]
[ 583-39-1 ]
[ 1131148-13-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With pyridine; at 20℃;Inert atmosphere;	General method: Benzimidazole-2-thiol (7) (1 eq) and pertinent acid chloride or acid anhydride (1.1 eq) were dissolved in pyridine (4.4 eq) under a nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature. After quenching with water (10-25 ml), ethyl acetate (30-45 ml) was added. The organic phase was extracted with 3M hydrochloric acid (3 × 25 ml), dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified as stated below.