[ CAS No. 3287-79-4 ] {[proInfo.proName]}

Name: 3287-79-4|5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione|95%
Brand: Ambeed
SKU: A216923
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Quality Control of [ 3287-79-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3287-79-4 ]

Product Details of [ 3287-79-4 ]

CAS No. :	3287-79-4	MDL No. :	MFCD00519115
Formula :	C₉H₁₀N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CKUXMYYDAQIJRQ-UHFFFAOYSA-N
M.W :	178.25	Pubchem ID :	2731017
Synonyms :

Calculated chemistry of [ 3287-79-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	2.0
Molar Refractivity :	53.42
TPSA :	63.67 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.97
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	2.84
Log Po/w (MLOGP) :	1.55
Log Po/w (SILICOS-IT) :	4.51
Consensus Log Po/w :	2.59

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.8
Solubility :	0.284 mg/ml ; 0.00159 mol/l
Class :	Soluble
Log S (Ali) :	-3.03
Solubility :	0.168 mg/ml ; 0.000942 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.79
Solubility :	0.0286 mg/ml ; 0.000161 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 3287-79-4 ]

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 [ 3287-79-4 ]

* 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 [ 3287-79-4 ]

[ 3287-79-4 ] Synthesis Path-Downstream 1~71

1
[ 78-95-5 ]
[ 3287-79-4 ]
[ 22902-38-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1969,vol. 5,p. 243 - 245
Khimiya Geterotsiklicheskikh Soedinenii,1969,vol. 5,p. 321 - 324

2
[ 70-11-1 ]
[ 3287-79-4 ]
[ 22902-44-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1969,vol. 5,p. 243 - 245
Khimiya Geterotsiklicheskikh Soedinenii,1969,vol. 5,p. 321 - 324

3
[ 3400-55-3 ]
[ 3287-79-4 ]
[ 18204-54-1 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1967,vol. 3,p. 709 - 712
Khimiya Geterotsiklicheskikh Soedinenii,1967,vol. 3,p. 899 - 903

4
[ 1484-50-0 ]
[ 3287-79-4 ]
[ 22902-48-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1969,vol. 5,p. 243 - 245
Khimiya Geterotsiklicheskikh Soedinenii,1969,vol. 5,p. 321 - 324

5
[ 107-20-0 ]
[ 3287-79-4 ]
[ 16458-71-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1967,vol. 3,p. 709 - 712
Khimiya Geterotsiklicheskikh Soedinenii,1967,vol. 3,p. 899 - 903

6
[ 1056477-06-5 ]
[ 3287-79-4 ]
[ 22902-53-0 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1969,vol. 5,p. 243 - 245
Khimiya Geterotsiklicheskikh Soedinenii,1969,vol. 5,p. 321 - 324

7
[ 3287-79-4 ]
[ 814-75-5 ]
[ 22902-41-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1969,vol. 5,p. 243 - 245
Khimiya Geterotsiklicheskikh Soedinenii,1969,vol. 5,p. 321 - 324

8
[ 29310-88-1 ]
[ 3287-79-4 ]
[ 78765-48-7 ]

Reference： [1]Archiv der Pharmazie,1981,vol. 314,p. 435 - 439

9
[ 140-89-6 ]
[ 3171-45-7 ]
[ 3287-79-4 ]

Yield	Reaction Conditions	Operation in experiment
62%		Example 1; Chemistry; 2-Mercapto-5,6-dimethylbenzimidazole. A mixture of 10 g of 4,5-dimethylphenylenediamine, 16 g of potassium ethyl xanthate, 100 mL ethanol and 14 mL of water were added to a 500 mL Erlenmeyer flask and heated to reflux. After 3 h, 3.4 g of charcoal (Norit A) was added and refluxed for an additional 10 min. The Norit was filtered and the filtrate was heated to 60-70 C. To the warm solution was added 100 mL of warm tap water and 8 mL of acetic acid in 16 mL of water with good stirring. Upon the addition of the acetic acid solution, the mixture became a foamy solid. The mixture was placed in a 4 C. refrigerator for 3 h. The solid was filtered and dried over P2O5 to give 8.1 g (62%) of a tan solid. The compound was used without further purification.

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 1517 - 1523
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 4793 - 4797
[3]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 900 - 907
[4]Patent: US2009/247520,2009,A1 .Location in patent: Page/Page column 15

10
[ 822-87-7 ]
[ 3287-79-4 ]
[ 22902-53-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 263 - 265

11
[ 125163-08-8 ]
[ 3287-79-4 ]
[ 104658-92-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 1517 - 1523

12
[ 353-83-3 ]
[ 3287-79-4 ]
[ 105771-23-1 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 726 - 729

13
[ 114059-99-3 ]
[ 3287-79-4 ]
[ 106747-43-7 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1215 - 1220

14
[ 30132-23-1 ]
[ 3287-79-4 ]
[ 76263-07-5 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 263 - 265

15
[ 112646-49-8 ]
[ 3287-79-4 ]
[ 112643-58-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 2109 - 2116

16
[ 3287-79-4 ]
[ 118-91-2 ]
[ 121830-23-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 1142 - 1143

19
[ 3287-79-4 ]
[ 287730-18-1 ]

Reference： [1]Archiv der Pharmazie,2000,vol. 333,p. 123 - 129
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 651 - 668

20
[ 75-15-0 ]
[ 3171-45-7 ]
[ 3287-79-4 ]

Reference： [1]Organic Preparations and Procedures International,2000,vol. 32,p. 401 - 405

21
[ 64648-13-1 ]
[ 3287-79-4 ]
[ 21303-54-8 ]

Reference： [1]Organic Preparations and Procedures International,2000,vol. 32,p. 401 - 405

22
[ 3171-45-7 ]
ArNH-CS-CN [ No CAS ]
[ 3287-79-4 ]

Reference： [1]Heteroatom Chemistry,2002,vol. 13,p. 291 - 298

23
[ 22115-41-9 ]
[ 3287-79-4 ]
2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In N-methyl-acetamide; water;	Example 20 Preparation of Compound No. 952 To <strong>[3287-79-4]5,6-dimethylbenzimidazole-2-thiol</strong> (713 mg, 4 mmol) in dimethylformamide (10 ml), triethylamine (836 mul, 6 mmol) and 2-bromomethylbenzonitrile (1176 mg, 6 mmol) were added. After stirring at 80 C. overnight, water was added to the mixture, followed by extraction with ethyl acetate. After the ethyl acetate phase was dried with anhydrous sodium sulfate, it was concentrated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to obtain 2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile (1159 mg, yield 99%).

Reference： [1]Patent: US2005/267148,2005,A1

24
[ 3287-79-4 ]
[ 106747-07-3 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1215 - 1220

25
[ 3287-79-4 ]
[ 105796-50-7 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 726 - 729

26
[ 3287-79-4 ]
[ 78765-52-3 ]

Reference： [1]Archiv der Pharmazie,1981,vol. 314,p. 435 - 439

27
[ 3287-79-4 ]
[ 104658-52-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1989,vol. 37,p. 1517 - 1523

28
[ 3287-79-4 ]
[ 16535-33-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1967,vol. 3,p. 709 - 712
Khimiya Geterotsiklicheskikh Soedinenii,1967,vol. 3,p. 899 - 903

29
[ 3287-79-4 ]
[ 18204-55-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1967,vol. 3,p. 709 - 712
Khimiya Geterotsiklicheskikh Soedinenii,1967,vol. 3,p. 899 - 903

30
[ 2969-81-5 ]
[ 3287-79-4 ]
[ 255398-13-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; In DMF (N,N-dimethyl-formamide); at 80℃; for 12.0h;	[0128] 35 mul (0.25 mmol) of triethylamine and 36 mul (0.25 mmol) of 4-bromobutanoate ethyl ester were added to 36 mg (0.20 mmol) of the obtained <strong>[3287-79-4]5,6-dimethylbenzimidazole-2-thiol</strong>. After stirring the resulting solution for 12 hours at 80 C., water was added followed by extraction with diethyl ether. After drying the diethyl ether phase with anhydrous magnesium sulfate, it was concentrated and residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 54 mg of the target compound (yield: 92%). Confirmation of the compound was carried out by identifying it from the molecular weight using LC-MS. [0129] Calculated value M=292.12, Measured value (M+H)+=293.40

Reference： [1]Patent: US2004/10004,2004,A1 .Location in patent: Page 21

31
[ 3171-45-7 ]
[ 3287-79-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With carbon disulfide; In pyridine; for 18.0h;Heating / reflux;	[0125] 40 ml (0.66 mmol) of carbon disulfide were added to a pyridine solution (40 ml) of 4.5 g (33 mmol) of 5,6-dimethylorthophenylenediamine. After stirring the resulting solution for 18 hours while refluxing under heating, water was added followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous magnesium sulfate, it was concentrated under reduced pressure and dried for 6 hours at 80 C. under reduced pressure to obtain 4.1 g of the target compound (yield: 70%). [0126] 1H-NMR (270 MHz, DMSO-d6) (ppm): 12.30 (br, 1H), 6.91 (s, 2H), 2.21 (s, 6H)
		EXAMPLE 100 6-[[(5,6-Dimethyl-1H-benzimidazol-2-yl)-thio]methyl]-2-pyridinamine Reaction of 30 g (0.22 mole) of 4,5-dimethyl-1,2-phenylenediamine with potassium ethylxanthate using the method described in Example 86 yielded 19 g of 5,6-dimethyl-2-mercaptobenzimidazole, as confirmed by the nmr and infrared spectra and by elemental analysis.
		EXAMPLE 14 2-[(imidazo[1,2-a]pyridin-8-ylmethyl)thio]-5,6-dimethyl-1H-benzimidazole STR23 Reaction of 30 g (0.22 mole) of 4,5-dimethyl-1,2-phenylenediamine with potassium ethylxanthate using the method described in Example 10 yielded 19 g of 5,6-dimethyl-2-mercaptobenzimidazole, as confirmed by the nmr and infrared spectra and by elemental analysis.

Reference： [1]Patent: US2004/10004,2004,A1 .Location in patent: Page 21
[2]Patent: US5945425,1999,A
[3]Patent: US4687775,1987,A

32
[ 7250-67-1 ]
[ 3287-79-4 ]
[ 173352-22-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	In sodium hydroxide; ethanol;	Example 13. 2-[2-(Pyrrolidino)ethylthio]-5,6-dimethylbenzimidazole (XIII) and its dihydrochloride were synthesised as described above. The compound XIII was obtained from 2,67 g (0,015 mol) <strong>[3287-79-4]2-mercapto-5,6-dimethylbenzimidazole</strong> and 2,9 g (0,017 mol) 2-(pyrrolidino)ethylchloridehydrochloride in the presence 1,35 g (0,034 mol) sodium hydroxide in 90% yield (4,0 g, counting on monohydrate), m.p. 115-116 C. (with decomp., from ethanol with water). 1H NMR (CDCl3), delta: 1,97 (4H, m, beta-H of pyrrolidine); 2,34 (6H, s, 2CH3); 2,72 (4H, m, -H of pyrrolidine); 3,02 (2H, m, CH2S); 3,19 (2H, m, CH2N); 7,18 (2H, broad s, ArH). Calcd for C15H21N3S*H2O: C 61,4; H 7,8; N 14,3; S 10,9; Found: C 61,4; H 7,8; N 14,5; S 10,9.

Reference： [1]Patent: US6376666,2002,B1

33
[ 74-96-4 ]
[ 3287-79-4 ]
[ 173352-10-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water;	2-Ethylthio-5,6-dimethylbenzimidazole (I). 0,65 g (6 mmol) Ethylbromide was added to a solution 0,89 g (0,005 mol) <strong>[3287-79-4]2-mercapto-5,6-dimethylbenzimidazole</strong> and 0,24 g (0,006 mol) sodium hydroxide in 1 ml of water and 10 ml of ethanol. The reaction mixture was refluxed for 1.5 hr before disappearing starting thione (control by using TLS), cooled and added water. The precipitated product was filtered off, washed with water and dried under atmospheric conditions. The yield was 0,91 g (88%) of compound I, m.p. 123-124 C. (from water-ethanol).1H NMR (CDCl3), delta: 1.37 (3H, t, CH2CH3); 2,32 (6H, s, 2CH3); 3,27 (2H, q, CH2CH3); 7,31 (2H, s, ArH).

Reference： [1]Patent: US6376666,2002,B1

34
[ 3287-79-4 ]
[ 106747-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In methanol;	EXAMPLE 9 2-[[(5,6-Dimethyl-1H-benzimidazol-2-yl)thio]methyl]benzenamine The title compound was prepared by the method of Example 1 using 2.56 g of <strong>[3287-79-4]5,6-dimethyl-2-mercaptobenzimidazole</strong> instead of 2-mercaptobenzimidazole and 2.56 g of 2-(chloromethyl) aniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline. Instead of using sodium carbonate in an extraction, the crude precipitate was neutralized with triethylamine in methanol. Trituration of the resultant crude title compound with methanol and diethyl ether gave 2.0 g of analytically pure title compound. Anal. Calc'd. for C15 H15 N3 S: C, 67.81; H, 6.05; N,14.83; S, 11.31. Found: C, 67.21; H, 6.16; N, 14.50; S, 11.06.

Reference： [1]Patent: US5945425,1999,A

35
[ 3287-79-4 ]
[ 118267-36-0 ]

Yield	Reaction Conditions	Operation in experiment
		The title compound (3.0 g) was prepared by the method of Example 84 using 3.5 g of <strong>[3287-79-4]5,6-dimethyl-2-mercaptobenzimidazole</strong> instead of 2-mercaptobenzimidazole. Structure assignment was supported by the nmr spectrum.

Reference： [1]Patent: US5945425,1999,A

Yield	Reaction Conditions	Operation in experiment
		Example A18 Synthesis of 1-(2'-(5',6'-dichlorobenzimidazolyl)thio)-5-(2"-(5",6"-dimethylbenzimidazolyl)thio)pentane (Compound A15) In the same manner as in Example A1, 5-(2'-(5',6'-dimethylbenzimidazolyl)thio)pentyl bromide (6.6 g) was obtained from 2-mercapto-5,6-dimethylbenzimidazole (5.34 g) and 1,5-dibromopentane (34.5 g).

37
[ 353-83-3 ]
[ 6674-22-2 ]
[ 3287-79-4 ]
[ 105771-23-1 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; water;	A mixture of <strong>[3287-79-4]5,6-dimethyl-2-mercaptobenzimidazole</strong> (9.45 g, 0.053 mole), 1,8-diazabicyclo [5.4.0] undec-7-ene (9.7 g, 0.064 mole) and 1-iodo-2,2,2-trifluroethane (13.4 g, 0 064 mole) in 210 ml dimethylformamide is heated (50 C. for 41/2 hours), poured onto ice and water (1500 ml), and the precipated solid collected by filtration and dried. The product is recrystallized from toluene-ligroine giving 5,6-dimethyl-2-(2,2,2-trifluoroethyl-mercapto)-1H-benzimidazole (3.4 g, 0.013 mole), m.p. 150-163 C.

Reference： [1]Patent: US4608381,1986,A

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 22 6-[[(5,6-dimethyl-1H-benzimidazol-2-yl)thio]methyl]-2-pyridinamine STR30 Reaction of 30 g (0.22 mole) of 4,5-dimethyl-1,2-phenylenediamine with potassium ethylxanthate using the method described in Example 8 yielded 19 g of 5,6-dimethyl-2-mercaptobenzimidazole, as confirmed by the nmr and infrared spectra and by elemental analysis.

39
ethereal HCl [ No CAS ]
2-(1,2-dibromoethyl)pyridine hydrobromide [ No CAS ]
[ 3287-79-4 ]
2,3-dihydro-6,7-dimethyl-2-(pyridin-2-yl)thiazolo[3,2-a]-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.35%	With sodium carbonate; In methanol; isopropyl alcohol;	EXAMPLE 9 2,3-Dihydro-6,7-dimethyl-2-(2-pyridyl)thiazolo[3,2-a]benzimidazole 2-(1,2-Dibromoethyl)pyridine hydrobromide (9.7 g) was added to <strong>[3287-79-4]5,6-dimethyl-2-mercaptobenzimidazole</strong> (5.3 g) in methanol (100 ml) and the mixture was heated at reflux for 18 hours, after which time the solvent was removed under reduced pressure. The residue was treated with saturated sodium carbonate solution and extracted into dichloromethane. The extracts were dried (MgSO4) and evaporated and the residue was purified by chromatography on silica using ethyl acetate as eluent. The solvent was removed under reduced pressure and the residue dissolved in hot propan-2-ol and ethereal HCl was added. The product obtained was recrystallized from methanol and ethyl acetate to give the title compound as the dihydrochloride, hemihydrate (0.75 g, 7.35%) mp 222 C. decomp. Analysis: Found: C, 53.0; H, 4.8; N, 11.3. C16 H15 N3 S.2HCl.1/2H2 O requires C, 52.9; H, 5.0; N, 11.6%.

Reference： [1]Patent: US4873237,1989,A

40
[ 3287-79-4 ]
[ 33095-53-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ammonium hydroxide; chlorine; In methanol; water;	EXAMPLE 7 Preparation of 2,4,7-trichloro-5,6-dimethylbenzimidazole. Ten grams (0.56 mole) of <strong>[3287-79-4]2-mercapto-5,6-dimethylbenzimidazole</strong> was suspended in a solution of 100 ml. of methanol and 200 ml. of concentrated hydrochloric acid. Chlorine was bubbled through the suspension while the temperature was maintained at about 25 to 30 C. by means of an ice bath. The chlorine saturated suspension was then warmed to a temperature of about 45 C. and after about 10 minutes a homogenous solution was formed. This solution was stirred at a temperature of about 45 C. for ten minutes and cooled to room temperature. A heavy precipitate was formed and the reaction mixture was diluted with 200 ml. of water. The pH of the mixture was adjusted to a pH of about 8 by the addition of ammonium hydroxide. The precipitate was filtered, washed with water and crystallized from ethanol-water to yield 2,4,7-trichloro-5,6-dimethylbenzimidazole melting at about 280-285 C.

Reference： [1]Patent: US4000275,1976,A

41
[ 41927-01-9 ]
[ 3287-79-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With carbon disulfide; In pyridine; water;	Reference Example 1. Preparation of 5,6-dimethylbenzimidazole-2-thiol To 5,6-dimethylorthophenylene diamine (4.5 g, 33 mmol) in pyridine (40 ml) was added carbon disulfide (40 ml, 0.66 mol). The resulting solution was heated to reflux under stirring for 18 hours, to which was added water, followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous magnesium sulfate, it was concentrated, and dried under reduced pressure at 80C for 6 hours to obtain the title compound (4.1 g, yield 70%).
70%	With carbon disulfide; In pyridine; water;	Reference Example 1 Preparation of 5,6-dimethylbenzimidazole-2-thiol To 5,6-dimethylorthophenylene diamine (4.5 g, 33 mmol) in pyridine (40 ml) was added carbon disulfide (40 ml, 0.66 mol). The resulting solution was heated to reflux under stirring for 18 hours, to which was added water, followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous magnesium sulfate, it was concentrated, and dried under reduced pressure at 80 C. for 6 hours to obtain the title compound (4.1 g, yield 70%). 1H-NMR (270 Mhz, DMSO-d6) (ppm): 12.30 (br, 1H), 6.91 (s, 2H), 2.21 (s, 6H)
70%	With pyridine; carbon disulfide; In water;	[Reference Example 1] Production of 5,6-dimethylbenzimidazole-2-thiol 40 ml (0.66 mmol) of carbon disulfide were added to a pyridine solution (40 ml) of 4.5 g (33 mmol) of 5,6-dimethylorthophenylenediamine. After stirring the resulting solution for 18 hours while refluxing under heating, water was added followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous magnesium sulfate, it was concentrated under reduced pressure and dried for 6 hours at 80C under reduced pressure to obtain 4.1 g of the target compound (yield: 70%). 1H-NMR (270 MHz, DMSO-d6) (ppm): 12.30 (br,1H), 6.91 (s,2H), 2.21 (s,6H)

Reference： [1]Patent: EP1097926,2001,A1
[2]Patent: US2005/267148,2005,A1
[3]Patent: EP1249450,2002,A1

42
[ 2417-73-4 ]
[ 255398-03-9 ]
[ 3287-79-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In N-methyl-acetamide; water;	Reference Example 2. Preparation of 2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzoic acid methyl ester To the resulting 5,6-dimethylbenzimidazole-2-thiol (89 mg, 0.50 mmol) in dimethylformamide (2 ml), triethylamine (84 mul, 0.6 mmol) and 2-bromomethyl benzoic acid methyl ester (137 mg, 0.6 mmol) were added. After the resulting solution was stirred at 80C for 1.5 hours, water was added, followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous magnesium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain the title compound (146 mg, yield 90%). The compound was confirmed by identification of molecular weight using LC-MS. Calculated M = 326.11, measured (M+H)+= 327.2
90%	With triethylamine; In N-methyl-acetamide; water;	Reference Example 2 Preparation of 2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzoic acid methyl ester To the resulting 5,6-dimethylbenzimidazole-2-thiol (89 mg, 0.50 mmol) in dimethylformamide (2 ml), triethylamine (84 mul, 0.6 mmol) and 2-bromomethyl benzoic acid methyl ester (137 mg, 0.6 mmol) were added. After the resulting solution was stirred at 80 C. for 1.5 hours, water was added, followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous magnesium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the title compound (146 mg, yield 90%). The compound was confirmed by identification of molecular weight using LC-MS.

Reference： [1]Patent: EP1097926,2001,A1
[2]Patent: US2005/267148,2005,A1

43
[ 111-24-0 ]
[ 3287-79-4 ]
1,5-bis(5,6-dimethyl-2-benzimidazoylthio)pentane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		(17) Synthesis of 1,5-bis(5,6-dimethyl-2-benzimidazoylthio)pentane (compound I-2): 3.9 g (yield: 93%) of the intended compound was obtained from 3.6 g of <strong>[3287-79-4]2-mercapto-5,6-dimethylbenzimidazole</strong> and 2.5 g of 1,5-dibromopentane in the same manner as in (1). Melting point: 188 to 191 C.; Elementary analysis for C23 H28 N4 S2: Calculated: C 65.05; H 6.65; N 13.20 (%); Found: C 65.20; H 6.52; N 13.36 (%)

Reference： [1]Patent: US5962493,1999,A

44
[ 3287-79-4 ]
[ 1189164-12-2 ]

Yield	Reaction Conditions	Operation in experiment
32%		2-Bromo-5,6-dimethylbenzimidazole (8). To a cooled solution of 40 mL of acetic acid and 4.2 mL of 48% aqueous HBr was added 5 g 1. To this slurry was added 5.2 mL of bromine dropwise slowly over 10 min. The reaction turned orange and became unstirrable after half of the bromine was added, manual or mechanical agitation was needed to break up solids. After the addition of the bromine, 80 mL of acetic acid was added and the mixture was stirred at room temperature. After 4.5 h, the mixture was diluted with 90 mL of water and cooled to 0 C. The pH of the mixture was adjusted to 4 by the addition of solid NaOH. Upon basification a solid precipitated out of solution. It was filtered and dried overnight to give 2 g (32%) of product as a light orange solid. 1H NMR (300 MHz, DMSO-d6) delta 2.25 (s, 6H), 7.20 (s, 2H). MS (ESI) calculated C9H9BrN2 m/z=223.99, 225.99 found m/z=225.24, 227.25 [M+H].

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4793 - 4797
[2]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 900 - 907
[3]Patent: US2009/247520,2009,A1 .Location in patent: Page/Page column 15

45
[ 90261-18-0 ]
[ 3287-79-4 ]
C₂₀H₂₉N₃S [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2011,vol. 81,p. 128 - 131

46
[ 125454-66-2 ]
[ 3287-79-4 ]
[ 847504-85-2 ]

Reference： [1]Russian Journal of General Chemistry,2011,vol. 81,p. 128 - 131

47
[ 125454-66-2 ]
[ 3287-79-4 ]
C₂₂H₂₅N₃S [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2011,vol. 81,p. 128 - 131

48
[ 3287-79-4 ]
[ 758679-97-9 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 900 - 907
[2]Patent: US2009/247520,2009,A1

49
[ 3287-79-4 ]
[ 758679-97-9 ]
[ 1224437-04-0 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 900 - 907

50
[ 3287-79-4 ]
[ 301163-47-3 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 900 - 907
[2]Patent: US2009/247520,2009,A1

51
[ 3287-79-4 ]
[ 1535187-00-8 ]
[ 1535187-25-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 651 - 668

52
[ 3287-79-4 ]
[ 1310963-71-3 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 651 - 668

53
[ 3287-79-4 ]
[ 1351617-12-3 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 651 - 668

54
[ 1438-16-0 ]
[ 3171-45-7 ]
[ 3287-79-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	In 5,5-dimethyl-1,3-cyclohexadiene;Heating;	General procedure: O-phenylenediamines (0.065 mol) was heated with N-aminorhodanine (0.065 mol) in xylene (50 ml) for 5 hours. The obtained residue was filtered and was crystallized from aqueous alcohol (charcoal). The obtained solid was recrystallized in ethanol.

Reference： [1]Oriental Journal of Chemistry,2016,vol. 32,p. 1765 - 1768

55
[ 637-44-5 ]
[ 3287-79-4 ]
7,8-dimethyl-2-phenyl-4H-benzo[4,5]imidazo[2,1-b][1,3]thiazin-4-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4515 - 4522

56
[ 583-60-8 ]
[ 3287-79-4 ]
4a,8,9-trimethyl-2,3,4,4a-tetrahydrobenzo[d]benzo[4,5]imidazo[2,1-b]thiazol-11a(1H)-ol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4979 - 4983

57
[ 78-84-2 ]
[ 3287-79-4 ]
2,2,6,7-tetramethyl-2,3-dihydrobenzo[4,5]imidazo[2,1-b]thiazol-3-ol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4979 - 4983

58
[ 119072-55-8 ]
[ 6630-33-7 ]
[ 3287-79-4 ]
C₂₄H₂₃N₅S [ No CAS ]