58533-15-6|2-Chloro-1-ethyl-1H-benzo[d]imidazole| Ambeed

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Quality Control of [ 58533-15-6 ] Purity: 97% SDS Specification

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Product Details of [ 58533-15-6 ]

CAS No. :	58533-15-6
Formula :	C₉H₉ClN₂
M.W :	180.63
SMILES Code :	CCN1C(Cl)=NC2=CC=CC=C12
MDL No. :	MFCD00769822
InChI Key :	IROJYPSJGGDBCD-UHFFFAOYSA-N
Pubchem ID :	3744796

Safety of [ 58533-15-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Application In Synthesis of [ 58533-15-6 ]

* 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 [ 58533-15-6 ]

[ 58533-15-6 ] Synthesis Path-Downstream 1~31

1
[ 110-91-8 ]
[ 58533-15-6 ]
[ 145326-37-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 2709 - 2712.

2
[ 10045-45-1 ]
[ 58533-15-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 2709 - 2712.

3
[ 36016-40-7 ]
[ 58533-15-6 ]
1-Amino-2-chlor-3-ethylbenzimidazol-1-ium-(mesitylen-2-sulfonat) [ No CAS ]

References: [1]Helvetica Chimica Acta,1986,vol. 69,p. 1521 - 1530.

4
[ 110-85-0 ]
[ 58533-15-6 ]
[ 145909-56-4 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 586 - 593.

7
[ 4857-06-1 ]
ethyl halide [ No CAS ]
[ 58533-15-6 ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 586 - 593.

8
[ 58533-15-6 ]
[ 107550-90-3 ]

References: [1]Helvetica Chimica Acta,1986,vol. 69,p. 1521 - 1530.

9
[ 23838-73-5 ]
[ 58533-15-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 2709 - 2712.

10
aqueous potassium carbonate [ No CAS ]
[ 10045-45-1 ]
[ 58533-15-6 ]

Yield	Reaction Conditions	Operation in experiment
86 g (77%)	With hydrogenchloride; In dichloromethane; trichlorophosphate;	A. 2-chloro-1-ethylbenzimidazole 1-Ethyl-2-benzimidazolinone (100 g, 0.62 mol) was dissolved in phosphorus oxychloride (475 mL) with stirring and heated to reflux temperature. Hydrogen chloride gas was passed into the refluxing solution for 4 h. Excess phosphorous oxychloride was removed on a rotary evaporator at 70 C. The residue was poured into a stirred mixture of aqueous potassium carbonate solution and methylene chloride. The mixture was basified with 50% sodium hydroxide solution and the methylene chloride layer was separated, dried (Na2 SO4), concentrated, and distilled to obtain 86 g (77%) of oil, bp 110-115 C./2-0.3 mmHg, which crystallized on standing; mp 50-52 C.

References: [1]Patent: US5106857,1992,A .

11
[ 4857-06-1 ]
[ 75-03-6 ]
[ 58533-15-6 ]

Yield	Reaction Conditions	Operation in experiment
10.0 g (61%)	With NaH; In N,N-dimethyl-formamide; mineral oil;	Step 1) Preparation of 2-Chloro-1-ethylbenzimidazole To a cooled (0 C.) stirred suspension of NaH (60% dispersion in mineral oil; 7.08 g, 0.118 mol) in DMF (100 mL) was added 2-chlorobenzimidazole (15.00 g, 0.098 mol). The mixture was warmed to room temperature and stirred for 1 hour. Ethyl iodide (18.40 g, 0.118 mol) was added and stirring was continued for 3 hours. The mixture was poured onto the ice water and the resulting off-white solid was collected by filtration to give 10.0 g (61%) of product m.p. 48-50 C. NMR (DMSO-d6, 300 MHz): delta1.3 (t, J=8.6 Hz, 3H), 4.28 (q, J=8.6 Hz, 2H), 7.25 (m, 2H), 7.60 (m, 2H).
		In an ice-bath,To a solution of 2-chloro-1H-benzo[d]imidazole (1.31 mmol) in N,N-dimethylformamide (6 mL) was added NaH (60% dispersion in paraffin, 1.57 mmol). after 20 minutes,Iodoethane (1.57 mmol) was added,The mixture was left at room temperature. 2 hours later,The reaction is quenched with water,Extraction with EtOAc (2x).The resulting organic phase is washed with brine,Dried over Na2SO4 and concentrated to give A2 as a yellow oil.

References: [1]Chemistry - A European Journal,2019,vol. 25,p. 12981 - 12990.
[2]Patent: US5149700,1992,A .
[3]Patent: KR2018/36412,2018,A .Location in patent: Paragraph 0103; 0107-0108.

12
[ 58533-15-6 ]
[ 139703-63-2 ]

Yield	Reaction Conditions	Operation in experiment
3.1 g (78%)	In N',N-dimethylethylendiamine; aqueous HOAc;	Step 2) Preparation of 2-[N-Methyl-N-[(2-methylamino)ethyl]amino]-1-ethyl-1H-benzimidazole A solution of <strong>[58533-15-6]2-chloro-1-ethylbenzimidazole</strong> (3.1 g, 0.0172 mol) in N,N'-dimethylethylendiamine (28 mL, 0.261 mol) was heated under reflux for 22 hours. The mixture was concentrated and dissolved in 10% aqueous HOAc (100 mL) and extracted with EtOAc. The aqueous phase was made basic (pH9) with solid KOH, satured with NaCl, and extracted with EtOAc. The extracts were dried (MgSO4) and concentrated to give 3.1 g (78%) of a brown oil. NMR (DMSO-d6, 300 MHz): delta1.31 (t, J=7.2, 3H), 2.29 (s, 3H), 2.71 (t, J=6.7, 2H), 2.92 (s, 3H), 3.28 (t, J=6.7, 2H), 4.10 (q, J=7.2, 2H), 7.05 (m, 2H), 7.34 (m, 2H).

References: [1]Patent: US5149700,1992,A .

13
[ 7791-89-1 ]
[ 58533-15-6 ]
1-ethyl-N-(1-ethyl-3-pyrrolidinyl)-1H-benzimidazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; butan-1-ol;	B. Title compound A solution of 11.4 g (0.1 mol) of 3-amino-1-ethylpyrrolidine and 14.4 g (0.08 mol) of <strong>[58533-15-6]2-chloro-1-ethylbenzimidazole</strong> in 40 mL of ethanol was heated at reflux for 72 h. A mass spectal analysis showed the reaction to be about 25% complete. The solution was concentrated on the rotary evaporator (60 C./30 mm) and the residue was dissolved in 50 mL of n-butanol. The solution was heated to reflux for 24 h and partitioned between CHCl3 and dilute NaOH. The CHCl3 solution was dried (Na2 SO4) and concentrated. The residue was chromatographed on the Waters Associates preparative HPLC (silica gel/isopropyl alcohol). The purified material was isolated as the fumarate salt by the following procedure. The collected material (6 g, 0.023 mol) was treated with 2.7 g, 0.023 mol) of fumaric acid. The resulting crystals weighed 3.5 g and melted at 189-191 C. Analysis: Calculated for C15 H22 N4.2C4 H4 O4: C, 56.32; H, 6.16; N, 11.42. Found: C, 56.22; H, 6.24; N, 11.48.

References: [1]Patent: US5106857,1992,A .

14
[ 4857-06-1 ]
[ 74-96-4 ]
[ 58533-15-6 ]

Yield	Reaction Conditions	Operation in experiment
92.7%		To a solution of 2-chloro-1H- benzo[d]imidazole (1 g, 6.553 mmol) in DMF (50 mL) was added NaH (340.8 mg, 8.519 mmol) at 0 oC. After 15 minutes, bromoethane (1.33 g, 8.519 mmol) was added to the reaction mixture at 0 oC. The reaction mixture was stirred at r.t. for 2 hours. TLC (Petroleum ether/EtOAc = 5/1; silica gel plate) showed complete consumption of the starting material after this time. The mixture was quenched by water at 0 oC. The reaction mixture was extracted with EtOAc (50 mL x 2), washed with brine and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified via column chromatography (Petroleum ether/EtOAc) to give the title compound (1.1 g, 92.7% yield) as a white solid. LC- MS: Calculated exact mass = 180.1; Found [M+H]+ = 181.1.
73%		General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.

References: [1]Patent: WO2019/140387,2019,A1 .Location in patent: Paragraph 00412; 00413.
[2]Zeitschrift fur Anorganische und Allgemeine Chemie,2013,vol. 639,p. 2450 - 2454.
[3]European Journal of Medicinal Chemistry,2011,vol. 46,p. 417 - 422.
[4]European Journal of Medicinal Chemistry,2010,vol. 45,p. 909 - 914.

15
[ 58533-15-6 ]
[ 90562-75-7 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 909 - 914.

16
[ 773837-37-9 ]
[ 58533-15-6 ]
[ 51579-39-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	In N,N-dimethyl-formamide; at 100℃; for 2h;	General procedure: 4 (8.7 mmol) was dissolved in dry DMF (15 mL), to the solution was added NaCN (9.2 mol), and the mixture was stirred for 2 h at 100 C. The mixture was poured into water (50 mL), filtrated, washed with water and dried to afford 5.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 417 - 422.

17
[ 4857-06-1 ]
[ 64-67-5 ]
[ 58533-15-6 ]

References: [1]Asian Journal of Chemistry,2012,vol. 24,p. 5756 - 5758,3.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 1210 - 1213.

18
[ 58533-15-6 ]
[ 39573-31-4 ]

Yield	Reaction Conditions	Operation in experiment
71.5%	With thiourea; In ethanol; for 12h;Reflux;	A solution of 2-chloro-1-ethyl-1H- benzo[d]imidazole (1.1 g, 6.111 mmol) in EtOH (50 mL) was treated with thiourea (697.6 mg, 9.167 mmol) at r.t. The reaction mixture was heated at reflux for 12 hours. TLC (Petroleum ether/EtOAc = 10/1; silica gel plate) showed complete consumption of the starting material after this time. The reaction mixture solvent was removed under reduced pressure and the mixture was purified via column chromatography (Petroleum ether/EtOAc) to give the title compound (778.1 mg, 71.5% yield) as a white solid. LC-MS: Calculated exact mass = 178.1; Found [M+H]+ = 179.1.
	With thiourea;Sealed tube; Microwave irradiation;	General procedure: A mixture of 4a-c (10 mM) and thiourea (0.76 g, 10 mM) was taken in a 10 mL CEM-reaction tube sealed by rubber stopper and subjected to microwave irradiation for 2 min at 130 C in a commercial microvawe reactor. After that, the tube was cooled and the completion of reaction was checked by TLC. Then the reaction mixture was poured into ice-cold water (50 mL). The separated solid was filtered, washed with water (2 x 10 mL) and dried. Yields are shown in Table I. The crude products were purified by recrystallization from ethyl acetate to obtain pure 5a-c, identical with the same products obtained above.

References: [1]Patent: WO2019/140387,2019,A1 .Location in patent: Paragraph 00412; 00414.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 1210 - 1213.

19
[ 14221-01-3 ]
[ 13826-83-0 ]
[ 58533-15-6 ]
trans-[PdCl((C₇H₅N₂)Et)(PPh₃)2]BF₄ [ No CAS ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2013,vol. 639,p. 2450 - 2454.

20
[ 13826-83-0 ]
[ 14221-02-4 ]
[ 58533-15-6 ]
cis/trans-[PtCl((C₇H₅N₂)Et)(PPh₃)2]BF₄ [ No CAS ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2013,vol. 639,p. 2450 - 2454.

21
[ 4857-06-1 ]
[ 623-81-4 ]
[ 58533-15-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2015,vol. 54B,p. 829 - 832.

22
[ 17356-08-0 ]
[ 58533-15-6 ]
[ 39573-31-4 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2015,vol. 54B,p. 829 - 832.

23
[ 2365-48-2 ]
[ 58533-15-6 ]
C₁₂H₁₄N₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In chloroform; at 60℃;	to chloroform (8 mL) was addedThe dissolved A2 (1.6 mmol)To the stirred solution was added methyl thiochlorolate (2.2 mmol) andTriethylamine (2.4 mmol) was added and the mixture was treated withAnd heated to 60 C overnight.The reaction mixture was diluted with chloroform,Washed with water, dried over Na2SO4,Lt; / RTI & gt;The crude residue was purified by flash column chromatography (n-hexane: EA = 5: 1 ratio) to prepare colorless oil A3.

References: [1]Patent: KR2018/36412,2018,A .Location in patent: Paragraph 0103; 0109-0110.

24
3-(4-(mercaptomethyl)-1-phenyl-1H-pyrazol-3-yl)-2H-chromen-2-one [ No CAS ]
[ 58533-15-6 ]
3-(4-(((1-ethyl-1H-benzo[d]imidazol-2-yl)thio)methyl)-1-phenyl-1H-pyrazol-3-yl)-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4h;	General procedure: A mixture of 10 (5 mM), 14 (5 mM) in DMF (20 mL) containing K2CO3 (2 mM) and TBAB (2 mM) was stirred at RT for a period of 3-5 h. The reaction was monitored by TLC analysis. After the completion of reaction, the mixture was poured into ice-cold water (30 mL). The separated solid was filtered, washed with water (2 9 10 mL) and dried. The crude product was recrystallized from ethanol to yield pure 13.

References: [1]Research on Chemical Intermediates,2018,vol. 44,p. 4455 - 4468.

25
[ 58533-15-6 ]
3-((1-ethyl-1H-benzo[d]imidazol-2-yl)thio)piperidine-2,6-dione [ No CAS ]

References: [1]Patent: WO2019/140387,2019,A1 .

26
[ 62-53-3 ]
[ 58533-15-6 ]
1-ethyl-N-(1-ethyl-1H-benzo[d]imidazol-2-yl)-N-phenyl-1H-benzo[d]imidazol-2-amine [ No CAS ]

References: [1]Chemistry - An Asian Journal,2020,vol. 15,p. 129 - 135.

27
[ 58533-15-6 ]
[ 2814-59-7 ]