Name: 1792-41-2|2,5-Dimethyl-1H-benzo[d]imidazole|95+%
Brand: Ambeed
SKU: A416592
Rating: 91 (26 reviews)

1
[ 60-35-5 ]
[ 636-24-8 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	at 180℃; im Rohr;

Reference： [1]Niementowski [Chemische Berichte, 1897, vol. 30, p. 3069]

2
[ 155221-39-9 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	beim Erhitzen;

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1902, vol. 35, p. 1259]

3
[ 24780-84-5 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	beim Erhitzen;

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1902, vol. 35, p. 1259]

4
[ 2818-63-5 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	beim Erhitzen zum Sieden;

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1901, vol. 34, p. 4204]

5
[ 1034250-03-7 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	beim Erhitzen zum Sieden;

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1901, vol. 34, p. 4204]

6
[ 612-45-3 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; tin
	With iron; acetic acid
	With palladium on activated charcoal; ethanol at 30℃; Hydrogenation;

	Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation 2: Erhitzen auf Temperaturen oberhalb des Schmelzpunktes
	Multi-step reaction with 2 steps 1: iron; acetic acid 2: 200 - 210 °C
	Multi-step reaction with 2 steps 1: ammonium sulfide 2: 150 °C
	Multi-step reaction with 2 steps 1: water; alcohol; acetic acid / gibt Eisenspaene in der Loesung 2: beim Destillieren

Reference： [1]Niementowski [Chemische Berichte, 1892, vol. 25, p. 864] Hobrecker [Chemische Berichte, 1872, vol. 5, p. 920]
[2]Boessneck [Chemische Berichte, 1886, vol. 19, p. 1757]
[3]Marks; Schultz [Journal of the American Chemical Society, 1951, vol. 73, p. 1368]
[4]Green; Day [Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170]
[5]Maron; Salzberg [Chemische Berichte, 1911, vol. 44, p. 3004]
[6]Bankiewicz [Chemische Berichte, 1889, vol. 22, p. 1399]
[7]Boessneck [Chemische Berichte, 1886, vol. 19, p. 1757]

7
[ 53476-34-9 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	bei der Destillation;
	at 150℃;
	at 200 - 210℃;

	With 4-methylisopropylbenzene
	With hydrogenchloride
	Erhitzen auf Temperaturen oberhalb des Schmelzpunktes;
	beim Destillieren;
	at 200 - 210℃;

Reference： [1]Boessneck [Chemische Berichte, 1886, vol. 19, p. 1757]
[2]Bankiewicz [Chemische Berichte, 1889, vol. 22, p. 1399]
[3]Maron; Salzberg [Chemische Berichte, 1911, vol. 44, p. 3004]
[4]Green; Day [Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170]
[5]Green; Day [Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170]
[6]Green; Day [Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170]
[7]Boessneck [Chemische Berichte, 1886, vol. 19, p. 1757]
[8]Maron; Salzberg [Chemische Berichte, 1911, vol. 44, p. 3004]

8
[ 43154-38-7 ]
[ 1792-41-2 ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 1167,1170
[2]Journal of the American Chemical Society,1942,vol. 64,p. 1167,1170
[3]Journal of the American Chemical Society,1942,vol. 64,p. 1167,1170

9
[ 85-44-9 ]
[ 1792-41-2 ]
[ 63786-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	at 200℃;

Reference： [1]Bamberger; Berle [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 315]

10
[ 1792-41-2 ]
[ 100-52-7 ]
[ 189056-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 200℃;
	at 200℃;

Reference： [1]Bamberger; Berle [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 315]
[2]Bamberger; Berle [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 315]

11
[ 1792-41-2 ]
[ 100-44-7 ]
[ 53811-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium ethanolate

Reference： [1]Bamberger; Lorenzen [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 289,296]

12
[ 1792-41-2 ]
[ 75-03-6 ]
[ 1034250-03-7 ]
1,3-diethyl-2,5-dimethyl-benzimidazolium; periodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 150℃; im Rohr;

Reference： [1]Huebner [Justus Liebigs Annalen der Chemie, 1881, vol. 210, p. 379]

13
[ 1792-41-2 ]
[ 75-03-6 ]
1,3-diethyl-2,5-dimethyl-benzimidazolium; periodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 200 - 230℃; im Rohr;

Reference： [1]Huebner [Justus Liebigs Annalen der Chemie, 1881, vol. 210, p. 379]

14
[ 1792-41-2 ]
[ 75-87-6 ]
2,2,2-trichloro-1-(2,5-dimethyl-benzimidazol-1-yl)-ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 100℃; im Rohr;

Reference： [1]Bamberger; Berle [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 360]

15
[ 1792-41-2 ]
[ 105-39-5 ]
(2,5-dimethyl-benzimidazol-1-yl)-acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate

Reference： [1]Bamberger; Lorenzen [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 289,296]

16
[ 1792-41-2 ]
[ 67-64-1 ]
2-(2,5-dimethyl-benzimidazol-1-yl)-propane-2-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur dioxide

Reference： [1]Boessneck [Chemische Berichte, 1888, vol. 21, p. 1909]

17
[ 1792-41-2 ]
[ 77-78-1 ]
[ 155221-39-9 ]

Reference： [1]Phillips [Journal of the Chemical Society, 1931, p. 1143,1153]

18
[ 1792-41-2 ]
[ 74-88-4 ]
[ 155221-39-9 ]
[ 24780-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol at 20℃;

Reference： [1]Fischer,O.; Roemer [Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2> 73, p. 434]

19
[ 1792-41-2 ]
[ 74-88-4 ]
[ 21337-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol at 20℃;
	With methanol at 120 - 130℃; im Rohr;

Reference： [1]Fischer,O.; Roemer [Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2> 73, p. 434]
[2]Bamberger; Lorenzen [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 289,296] Niementowski [Chemische Berichte, 1887, vol. 20, p. 1884]

20
[ 1792-41-2 ]
4,5,7-trichloro-2,6-dimethyl-1⁽³⁾H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; calcium chloride

Reference： [1]Bamberger; Lorenzen [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 289,296]

21
[ 1792-41-2 ]
[ 120209-26-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sulfuric acid; nitric acid In water at 0 - 5℃; for 1h;
	With nitric acid

Reference： [1]Benchidmi, M.; Kihel, A. El; Essassi, E. M.; Knouzi, N.; Toupet, L.; et al. [Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 10, p. 605 - 612]
[2]Ladenburg [Chemische Berichte, 1875, vol. 8, p. 677] Fischer,O.; Hess [Chemische Berichte, 1903, vol. 36, p. 3972] Niementowski [Chemische Berichte, 1886, vol. 19, p. 717] Maron; Salzberg [Chemische Berichte, 1911, vol. 44, p. 3004]

22
[ 1792-41-2 ]
[ 96048-73-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; calcium chloride at 0 - 5℃;

Reference： [1]Bamberger; Lorenzen [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 289,296]

23
[ 1792-41-2 ]
[ 147021-92-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sulfuric acid; nitric acid In water at 0 - 5℃; for 1h;
	With sodium nitrate; sulfuric acid
	With sulfuric acid; potassium nitrate

	Multi-step reaction with 2 steps 1: 74 percent / 92percent H₂SO₄, 1 equiv. 65percent HNO₃ / H₂O / 1 h / 0 - 5 °C 2: 92percent H₂SO₄, 3 equiv. 65percent HNO₃ / H₂O / 1 h / 0 - 5 °C
	With sodium nitrate; sulfuric acid
	With sulfuric acid; potassium nitrate

Reference： [1]Benchidmi, M.; Kihel, A. El; Essassi, E. M.; Knouzi, N.; Toupet, L.; et al. [Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 10, p. 605 - 612]
[2]Maron [Chemisches Zentralblatt, 1915, vol. 86, # I, p. 580]
[3]Maron [Chemisches Zentralblatt, 1915, vol. 86, # I, p. 580]
[4]Benchidmi, M.; Kihel, A. El; Essassi, E. M.; Knouzi, N.; Toupet, L.; et al. [Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 10, p. 605 - 612]
[5]Current Patent Assignee: Maron - DE282374, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 133][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 133]
[6]Current Patent Assignee: Maron - DE282374, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 133][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 133]

24
[ 1792-41-2 ]
4-bromo-2,5-dimethyl-1⁽³⁾H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; acetic acid
	With carbon disulfide; bromine
	With chloroform; bromine

Reference： [1]Niementowski [Chemische Berichte, 1892, vol. 25, p. 864]
[2]Niementowski [Chemische Berichte, 1892, vol. 25, p. 864]
[3]Bamberger; Berle [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 360]

25
[ 1792-41-2 ]
[ 709-19-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1893,vol. 273,p. 315
[2]Zhurnal Obshchei Khimii,1953,vol. 23,p. 835,837;engl.Ausg.S.873,875

26
[ 5433-07-8 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	bei der Destillation;

Reference： [1]Bistrzycki; Ulffers [Chemische Berichte, 1890, vol. 23, p. 1878]

27
[ 39623-57-9 ]
[ 1792-41-2 ]
[ 141-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 107 - 116℃;

Reference： [1]Witt [Chemische Berichte, 1886, vol. 19, p. 2977] Ladenburg; Ruegheimer [Chemische Berichte, 1879, vol. 12, p. 953]

28
[ 108-24-7 ]
[ 496-72-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate

Reference： [1]Noelting; Witt [Chemische Berichte, 1884, vol. 17, p. 78]

29
[ 75-07-0 ]
[ 496-72-0 ]
[ 1034250-03-7 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid

Reference： [1]Hinsberg [Chemische Berichte, 1887, vol. 20, p. 1589]

31
[ 496-72-0 ]
[ 75-36-5 ]
[ 1792-41-2 ]

Reference： [1]Bistrzycki; Cybulski [Chemische Berichte, 1891, vol. 24, p. 633]

32
[ 534-26-9 ]
[ 496-72-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	In various solvent(s) Heating;

Reference： [1]Butler, Richard N.; Fitzgerald, Kevin J. [Journal of the Chemical Society. Perkin transactions I, 1989, p. 155 - 157]

33
[ 1792-41-2 ]
[ 120209-26-9 ]
[ 147021-92-9 ]
[ 90349-14-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 8% 2: 17% 3: 31%	With sulfuric acid; nitric acid at 0 - 20℃;
1: 31% 2: 17%	With sulfuric acid; nitric acid at 0 - 20℃;

Reference： [1]Tian; Grivas [Synthesis, 1992, # 12, p. 1283 - 1286]
[2]Tian; Grivas [Synthesis, 1992, # 12, p. 1283 - 1286]

34
[ 1076-59-1 ]
[ 496-72-0 ]
[ 1792-41-2 ]
[ 64376-02-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetic acid at 90℃;

Reference： [1]Rao; Reddy; Veeranagaiah [Synthesis, 1992, # 5, p. 446 - 448]

35
[ 39214-83-0 ]
[ 496-72-0 ]
[ 1792-41-2 ]
[ 142335-32-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	In acetic acid at 90℃;

Reference： [1]Rao; Reddy; Veeranagaiah [Synthesis, 1992, # 5, p. 446 - 448]

36
[ 496-72-0 ]
[ 25755-82-2 ]
[ 1792-41-2 ]
[ 142335-30-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	In acetic acid at 90℃;

Reference： [1]Rao; Reddy; Veeranagaiah [Synthesis, 1992, # 5, p. 446 - 448]

37
[ 496-72-0 ]
[ 25755-85-5 ]
[ 1792-41-2 ]
[ 142335-31-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	In acetic acid at 90℃;

Reference： [1]Rao; Reddy; Veeranagaiah [Synthesis, 1992, # 5, p. 446 - 448]

38
[ 496-72-0 ]
[ 123-54-6 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With water; toluene-4-sulfonic acid In acetonitrile at 80℃; for 16h; Sealed tube;
84%	With sodium iodide dichloride In tetrahydrofuran; water Reflux;	2.2 General procedure for the synthesis of2-substituted 1,3-Benzazoles 3, 5 and 7 General procedure: To a mixture of o-substituted (-NH2 or -SH or -OH) anilines(1.0 mmol) and appropriate 1,3-diketones (1.1 mmol) in THF(5 mL) was added 30%w/w aqueous NaICl2 (0.2 mmol, 20mol%). The reaction was allowed to remain stirred at refluxtemperature for 2-3 h. After the reaction was complete, asindicated by TLC, the mixture was cooled to room temperature.The volatiles were removed under reduced pressureand treated successively with aqueous sodium thiosulphatesolution and saturated solution of NaHCO3, and extractedby ethylacetate (2×10 mL). The combined organic phaseswere washed with brine and dried over Na2SO4 and evaporatedunder vacuum. The crude reaction mixture was purifiedby column chromatography on silica gel using petroleumether/ethyl acetate as eluents.
58%	With hydrogenchloride In ethanol Heating;

Reference： [1]Mayo, Muhammad Shareef; Yu, Xiaoqiang; Zhou, Xiaoyu; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming [Organic Letters, 2014, vol. 16, # 3, p. 764 - 767]
[2]Bhagat, Saket B; Ghodse, Shrikant M; Telvekar, Vikas N [Journal of Chemical Sciences, 2018, vol. 130, # 1]
[3]Tian; Grivas [Synthesis, 1992, # 12, p. 1283 - 1286]

39
[ 496-72-0 ]
[ 31709-47-4 ]
[ 1792-41-2 ]
[ 65958-38-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	In acetic acid at 90℃;

Reference： [1]Rao; Reddy; Veeranagaiah [Synthesis, 1992, # 5, p. 446 - 448]

40
[ 141-97-9 ]
[ 496-72-0 ]
[ 1792-41-2 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	With Montmorillonite KSF In solid at 133℃; for 0.0666667h; Irradiation;

Reference： [1]Bougrin, Khalid; Soufiaoui, Mohamed [Tetrahedron Letters, 1995, vol. 36, # 21, p. 3683 - 3686]

41
[ 141-97-9 ]
[ 496-72-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With bentonite K₁₀ clay In benzene for 16h; Heating;

Reference： [1]Eynde, Jean Jacques Vanden; Mayence, Annie; Lor, Pascal; Haverbeke, Yves Van [Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 6, p. 387 - 392]

42
[ 70254-61-4 ]
[ 496-72-0 ]
[ 5400-75-9 ]
[ 1792-41-2 ]
4-acetonylidene-7-methyl-1,5-benzodiazepin-2-one [ No CAS ]
4-acetonylidene-8-methyl-1,5-benzodiazepin-2-one [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1997,vol. 106,p. 205 - 210

43
[ 1792-41-2 ]
6⁽⁵⁾-chloro-2,5⁽⁶⁾-dimethylbenzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With N-chloro-succinimide In chloroform for 2h; Heating;

Reference： [1]El Kihel, Abdellatif; Benchidmi, Mohamed; Essassi, El Mokhtar; Danion-Bougot, Renée [Synthetic Communications, 1999, vol. 29, # 3, p. 387 - 397]

44
[ 1792-41-2 ]
5,6-dibromo-2,5⁽⁶⁾-dimethylbenzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With bromine In acetic acid 1) reflux, 30 min; 2) rt, 2 h; further reagent;

Reference： [1]El Kihel, Abdellatif; Benchidmi, Mohamed; Essassi, El Mokhtar; Danion-Bougot, Renée [Synthetic Communications, 1999, vol. 29, # 3, p. 387 - 397]

45
[ 1792-41-2 ]
[ 74-88-4 ]
[ 24780-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol at 120 - 130℃; im Rohr;

Reference： [1]Bamberger; Lorenzen [Justus Liebigs Annalen der Chemie, 1893, vol. 273, p. 289,296]

46
[ 1792-41-2 ]
[ 74-88-4 ]
[ 24780-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol at 20℃;

Reference： [1]Fischer,O.; Roemer [Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2> 73, p. 434]

Yield	Reaction Conditions	Operation in experiment
	at 100℃;

Yield	Reaction Conditions	Operation in experiment
	at 107 - 120℃;

Yield	Reaction Conditions	Operation in experiment
	With zinc at 270℃;

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium

51
2,6-dimethyl-3H-benzimidazole-1-oxide [ No CAS ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	at 270℃;

Reference： [1]Bankiewicz [Chemische Berichte, 1889, vol. 22, p. 1399]

52
N-(5-methyl-2-nitro-phenyl)-acetimidic acid methyl ester [ No CAS ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With ammonium sulfate; magnesium In methanol at 60℃; for 0.5h;

Reference： [1]Harizi, Abdallah; Zantour, Hedi [Synthetic Communications, 2002, vol. 32, # 3, p. 387 - 392]

53
[ 77900-13-1 ]
[ 496-72-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
89.2%	With silica gel for 0.0833333h; microwave irradiation;

Reference： [1]Rostamizadeh; Derafshian [Journal of Chemical Research - Part S, 2001, # 6, p. 227 - 228]

54
[ 78-39-7 ]
[ 496-72-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With nano-Ni(II)/Y zeolite catalyst In neat (no solvent) at 60℃; for 0.766667h; Green chemistry;
97%	With mesoporous anchored Cu(II) Schiff-base complex from salicylaldehyde and (3-aminopropyl)trimethoxysilane In neat (no solvent) at 80℃; Green chemistry;	General procedure for the preparation of benzimidazole derivatives General procedure: A mxiture of phenylenediamine (1 mmol) with triethylorthoformate (1 mmol) in the presence of Cu/SBA15 as catalyst (0.0012 mmol) was stirred at 80 °C for 5 h under solvent free conditions. After completion of the reaction, the mixture was cooled to room temperature, and the mixture was washed with ethanol (20 mL) and the product was purified by crystallization or column chromatography to afford the final products.
96%	With [PVP-SO₃H] HSO₄ at 60℃; for 0.0666667h;	General procedure for the preparation of benzimidazole, benzoxazole, andbenzothiazole derivatives General procedure: o-Phenylenediamine, o-aminophenol or o-aminothiophenol (1 mmol), ortho esters(1.5 mmol) and [PVP-SO3H] HSO4 (7 mg, 4 mol %) were mixed and the resulting mixturewas stirred at 60 C for the appropriate time (Table 2). After completion of thereaction, as indicated by TLC (EtOAc:n-hexane; 1:3), ethyl acetate (10 mL) was addedand the catalyst was separated by filtration. The organic phase was washed with water,and then the organic phase was dried by Na2SO4. After filtration of the drying agent,ethyl acetate was removed under reduced pressure to get the desired product. The spectraldata of representative compounds follow.

95%	With ammonium chloride In water Inert atmosphere; Reflux; Green chemistry;
93%	With zirconium(IV) oxychloride octahydrate for 0.0833333h; Microwave irradiation;
93%	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 85℃; for 0.1h;
93%	With gallium(III) triflate at 20℃; for 0.183333h;
92%	With silica supported fluoroboric acid at 80℃; for 0.833333h; Neat (no solvent);
90%	at 90℃; for 1h;
90%	With tris(trifluoroacetato)bismuth(III) at 85℃; for 0.0833333h;
89%	With o-benzenedisulfonimide In neat (no solvent) at 20 - 25℃; for 4h; Green chemistry;
89%	With TiO₂ modified with bis-3-(trimethoxysilylpropyl)-ammonium hydrogen sulfate In neat (no solvent) at 90℃; for 0.25h;
79%	With mesoporous nanocomposite of Fe₃O₄ and -NHSO₃H functionalized silica (MCM-41) In neat (no solvent) at 90℃; for 0.5h;	General procedure for the synthesis of benzimidazole, benzoxazole, andbenzothiazole derivatives 2(a-o) General procedure: To a mixture of 1,2-phenylenediamine, 2-aminophenol, or 2-aminothiophenol, asappropriate (1 mmol), and the desired ortho ester (trimethyl orthoformate, triethylorthoformate, or triethyl orthoacetate) (1.5 mmol), in neat conditions, Fe3O4MCM-41NH-SO3H (0.03 g) was added and the resulting mixture was stirred in an oil bath at90 C for the proper time as determined by TLC [EtOAc: n-hexane (1:2)]. After endingthe reaction, ethyl acetate (20 mL) was added and the catalyst was separated by an externalmagnet. The organic phase was washed with brine and dried over Na2SO4. After filtration,the solvent was removed from the product under reduced pressure to obtainthe pure product. In some cases, the product was purified by recrystallization from nhexane.The known compounds were identified by matching their IR and NMR datawith literature values from the references cited, as well as melting points for those compoundswhich were solids. For the sake of completeness, the spectral data of some representativecompounds follow.

Reference： [1]Mobinikhaledi; Zendehdel; Goudarzi; Bardajee, G. Rezanejade [Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2016, vol. 46, # 10, p. 1526 - 1531]
[2]Ghaedi, Aseyeh; Goudarzi, Farideh; Hekmat, Shohreh; Rezanejade Bardajee, Ghasem [Inorganic and Nano-Metal Chemistry, 2022]
[3]Roudsari, Fatemeh Pakpour; Seddighi, Mohadeseh; Shirini, Farhad; Tajik, Hassan [Organic Preparations and Procedures International, 2020, p. 1 - 14]
[4]Fortenberry, Chelsea; Nammalwar, Baskar; Bunce, Richard A. [Organic Preparations and Procedures International, 2013, vol. 45, # 1, p. 57 - 65]
[5]Location in patent: experimental part Sanjeeva Reddy; Nagaraj [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 7, p. 1154 - 1159]
[6]Location in patent: experimental part Hojati, Seyedeh Fatemeh; Maleki, Behrooz; Beykzadeh, Zahra [Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 87 - 91]
[7]Location in patent: experimental part Liu, Juyan; Liu, Qian; Xu, Wei; Wang, Weilu [Chinese Journal of Chemistry, 2011, vol. 29, # 8, p. 1739 - 1744]
[8]Location in patent: experimental part Patil, Abasaheb V.; Bandgar, Babasaheb P.; Lee, Soo-Hyoung [Bulletin of the Korean Chemical Society, 2010, vol. 31, # 6, p. 1719 - 1722]
[9]Wang, Limin; Sheng, Jia; Tian, He; Qian, Changtao [Synthetic Communications, 2004, vol. 34, # 23, p. 4265 - 4272]
[10]Mohammadpoor-Baltork, Iraj; Khosropour, Ahmad R.; Hojati, Seyedeh F. [Monatshefte fur Chemie, 2007, vol. 138, # 7, p. 663 - 667]
[11]Barbero, Margherita; Cadamuro, Silvano; Dughera, Stefano [ARKIVOC, 2012, vol. 2012, # 9, p. 262 - 279]
[12]Mazloumi; Shirini; Goli-Jolodar; Seddighi [New Journal of Chemistry, 2018, vol. 42, # 8, p. 5742 - 5752]
[13]Pourhasan-Kisomi, Reyhaneh; Shirini, Farhad; Golshekan, Mostafa [Organic Preparations and Procedures International, 2021, vol. 53, # 2, p. 166 - 175]

55
[ 1445-45-0 ]
[ 496-72-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	In acetonitrile at 20℃; for 0.3h;
92%	With aminosulfonic acid In methanol at 20℃; for 0.5h;
90%	at 90℃; for 1h;

90%	With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 2h; chemoselective reaction;
90%	With silica choride at 80℃; for 0.166667h;
90%	With tungstate sulfuric acid In neat (no solvent) at 80℃; for 0.583333h; Green chemistry;

Reference： [1]Zhang, Zhan-Hui; Li, Jian-Jiong; Gao, Yuan-Zhe; Liu, Yu-Heng [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 6, p. 1509 - 1512]
[2]Zhang, Zhan-Hui; Li, Tong-Shuang; Li, Jian-Jiong [Monatshefte fur Chemie, 2007, vol. 138, # 1, p. 89 - 94]
[3]Wang, Limin; Sheng, Jia; Tian, He; Qian, Changtao [Synthetic Communications, 2004, vol. 34, # 23, p. 4265 - 4272]
[4]Location in patent: experimental part Khaksar, Samad; Heydari, Akbar; Tajbakhsh, Mahmood; Vahdat, Seyed Mohammad [Journal of Fluorine Chemistry, 2010, vol. 131, # 12, p. 1377 - 1381]
[5]Location in patent: experimental part Karami, Bahador; Ghashghaee, Vahideh; Khodabakhshi, Saeed [Chinese Journal of Chemistry, 2012, vol. 30, # 4, p. 959 - 964]
[6]Karami, Bahador; Khodabakhshi, Saeed; Haghighijou, Zahra [Chemical Papers, 2012, vol. 66, # 7, p. 684 - 690]

56
[ 6974-32-9 ]
[ 1792-41-2 ]
C₃₅H₃₀N₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tin(IV) chloride In 1,2-dichloro-ethane for 5h; Heating;

Reference： [1]Ji, Qi; Li, Jinliang; Ding, Fei; Han, Jie; Pang, Meili; Liu, Shuangxi; Meng, Jiben [Tetrahedron, 2006, vol. 62, # 11, p. 2529 - 2536]

57
[ 507453-85-2 ]
[ 75-07-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
33%	In ethanol for 24h; Heating;

Reference： [1]Wallace, Jeffery M.; Soederberg, Bjoern C. G.; Hubbard, Jeremiah W. [Synthetic Communications, 2006, vol. 36, # 22, p. 3425 - 3439]

58
[ 1792-41-2 ]
2,5-dimethyl-1-(β-D-erythropentofuranosyl)-1H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SnCl₄ / 1,2-dichloro-ethane / 5 h / Heating 2: 0.57 g / NH₃ / methanol

Reference： [1]Ji, Qi; Li, Jinliang; Ding, Fei; Han, Jie; Pang, Meili; Liu, Shuangxi; Meng, Jiben [Tetrahedron, 2006, vol. 62, # 11, p. 2529 - 2536]

59
[ 1792-41-2 ]
6⁽⁵⁾-bromo-2,5⁽⁶⁾-dimethyl-4⁽⁷⁾-nitrobenzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 60 percent / Br₂ / acetic acid / 1) reflux, 30 min; 2) rt, 2 h; further reagent 2: aq. HNO₃ (42 percent), aq. H₂SO₄ (92 percent) / 1 h / 0 - 5 °C

Reference： [1]El Kihel, Abdellatif; Benchidmi, Mohamed; Essassi, El Mokhtar; Danion-Bougot, Renée [Synthetic Communications, 1999, vol. 29, # 3, p. 387 - 397]

60
[ 1792-41-2 ]
6⁽⁵⁾-bromo-2,5⁽⁶⁾-dimethyl-7⁽⁴⁾-nitrobenzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 60 percent / Br₂ / acetic acid / 1) reflux, 30 min; 2) rt, 2 h; further reagent 2: aq. HNO₃ (42 percent), aq. H₂SO₄ (92 percent) / 1 h / 0 - 5 °C

Reference： [1]El Kihel, Abdellatif; Benchidmi, Mohamed; Essassi, El Mokhtar; Danion-Bougot, Renée [Synthetic Communications, 1999, vol. 29, # 3, p. 387 - 397]

61
[ 7418-36-2 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium / Hydrogenation 2: cymene

Reference： [1]Green; Day [Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170]

62
[ 58010-91-6 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bei der Reduktion 2: sodium acetate

Reference： [1]Noelting; Witt [Chemische Berichte, 1884, vol. 17, p. 78]

63
[ 89-62-3 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 2: palladium; ethanol / Hydrogenation 3: Erhitzen auf Temperaturen oberhalb des Schmelzpunktes

Reference： [1]Green; Day [Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170]

64
[ 1792-41-2 ]
2'-methyl-1H,1'(3')H-[2,5']bibenzimidazolyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: CrO₃; aqueous H₂SO₄ 2: aqueous HCl / 200 °C

Reference： [1]Porai-Koschiz et al. [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 835,837;engl.Ausg.S.873,875]

65
[ 1792-41-2 ]
5,2'-dimethyl-1⁽³⁾H,1'(3')H-[2,5']bibenzimidazolyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: CrO₃; aqueous H₂SO₄ 2: aqueous HCl / 200 °C

Reference： [1]Porai-Koschiz et al. [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 835,837;engl.Ausg.S.873,875]

66
[ 95-63-6 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: bei der Destillation

Reference： [1]Bistrzycki; Ulffers [Chemische Berichte, 1890, vol. 23, p. 1878]

67
[ 742054-04-2 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: beim Erhitzen zum Sieden

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1901, vol. 34, p. 4204]

68
[ 115835-41-1 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: beim Erhitzen zum Sieden

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1901, vol. 34, p. 4204]

69
[ 102871-93-2 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: water / 160 °C 2: tin; hydrochloric acid / Behandeln mit Eisessig 3: beim Erhitzen
	Multi-step reaction with 4 steps 1: alcohol; ammonia / 165 - 170 °C 2: tin; hydrochloric acid 4: beim Erhitzen zum Sieden

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1902, vol. 35, p. 1259]
[2]Fischer,O.; Rigaud [Chemische Berichte, 1901, vol. 34, p. 4204]

70
[ 502178-78-1 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tin; hydrochloric acid 3: beim Erhitzen zum Sieden

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1901, vol. 34, p. 4204]

71
[ 65081-42-7 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tin; hydrochloric acid / Behandeln mit Eisessig 2: beim Erhitzen

Reference： [1]Fischer,O.; Rigaud [Chemische Berichte, 1902, vol. 35, p. 1259]

72
[ 1792-41-2 ]
[ 114772-38-2 ]
[ 943859-85-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: 2,5-dimethylbenzimidazole With sodium hydride In toluene for 0.0833333h; Heating; Stage #2: Methyl 4'-(bromomethyl)biphenyl-2-carboxylate In toluene for 5h; Heating; Further stages.;

Reference： [1]Al-Azmi, Amal; George, Paulson; El-Dusouqui, Osman M. E. [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 3, p. 515 - 520]

73
[ 614-83-5 ]
[ 124-42-5 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 90 - 120℃; for 72h;

Reference： [1]Yang, Daoshan; Fu, Hua; Hu, Liming; Jiang, Yuyang; Zhao, Yufen [Journal of Organic Chemistry, 2008, vol. 73, # 19, p. 7841 - 7844]

74
[ 78-39-7 ]
[ 89-62-3 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃;

Reference： [1]Location in patent: scheme or table Liu, Zheng; Li, Haihong; Zhao, Qingjie; Shen, Jingshan [Heterocycles, 2008, vol. 75, # 8, p. 1907 - 1911]

75
[ 141-97-9 ]
[ 496-72-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With ytterbium(III) chloride In ethanol at 20℃; for 24h;
95%	With 1-n-butyl-3-methylimidazolim bromide In neat (no solvent) at 120℃; for 1h;	(b) For benzimidazole derivatives General procedure: A stirred mixture of aromatic diamine (1mmol) and β-ketoester or β-ketoamide (1mmol) was heated under inert condition at 120°C in the presence of 10mol% of ionic liquid III. After completion of reaction as revealed by TLC, product was crystallized from ethyl acetate-hexane or passes through short pad silica-gel to remove any colour impurities from the product to obtain analytically pure benzimidazoles.
88%	With ammonium bromide In methanol at 85℃; for 0.75h;

85%

With gadolinium(III) chloride hexahydrate at 80℃; for 3.5h;

General procedure for the synthesis of 2-substituted benzimidazoles General procedure: To a mixture of o-aromatic diamines (200 mg, 1.85 mmol) and 1,3-dicarbonyl compound (722 mg, 5.55 mmol), GdCl3*6H2O (25 mg, 0.09 mmol) was added and the mixture was stirred at 80°C for 3.0 hr. After completion of the reaction (TLC), the reaction mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the corresponding 2-methyl benzimidazole. The crude material was further purified by through column chromatography by using 10% ethyl acetate in hexane.

Reference： [1]Location in patent: experimental part Cai, Lijian; Ji, Xiaofeng; Yao, Zhigang; Xu, Fan; Shen, Qi [Chinese Journal of Chemistry, 2011, vol. 29, # 9, p. 1880 - 1886]
[2]Chakraborty, Ankita; Majumdar, Swapan; Maiti, Dilip K. [Tetrahedron Letters, 2016, vol. 57, # 30, p. 3298 - 3302]
[3]Location in patent: experimental part Raju, B. China; Theja, N. Dharma; Kumar, J. Ashok [Synthetic Communications, 2009, vol. 39, # 1, p. 175 - 188]
[4]Sathaiah; Venkat Lingaiah; Chandra Shekhar; Ravi Kumar; Raju; Shanthan Rao [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 8, p. 953 - 957]

76
[ 64-17-5 ]
[ 496-72-0 ]
[ 1792-41-2 ]

Yield	Reaction Conditions	Operation in experiment
94 %Chromat.	at 29.84℃; for 12h; Irradiation; Inert atmosphere;
49 %Chromat.	With air; silver-loaded TiO₂/montmorillonite K₁₀ In acetonitrile for 6h; Solar light irradiation;

Reference： [1]Shiraishi, Yasuhiro; Sugano, Yoshitsune; Tanaka, Shunsuke; Hirai, Takayuki [Angewandte Chemie - International Edition, 2010, vol. 49, # 9, p. 1656 - 1660]
[2]Location in patent: experimental part Selvam, Kaliyamoorthy; Annadhasan, Mari; Velmurugan, Rengasamy; Swaminathan, Meenakshisundaram [Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837]

77
[ 1792-41-2 ]
bis(4-(dimethylamino)phenyl)methylium tetrafluoroborate [ No CAS ]
BF₄^(1-)*C₂₆H₃₀N₄*H⁽¹⁺⁾ [ No CAS ]
BF₄^(1-)*C₂₆H₃₀N₄*H⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 20℃; Inert atmosphere;