Conditions | Yield |
---|---|
With sodium tetrahydroborate; tin bis(1,2-benzenethiolate) In tetrahydrofuran; phosphate buffer at 10℃; for 0.5h; pH=10; Reduction; | 100% |
With dibutyltin In benzene at 40℃; for 2h; other reagents; | 98% |
With acetic acid In dichloromethane at 20℃; for 2h; Irradiation; |
Conditions | Yield |
---|---|
In methanol; water at 20 - 60℃; Inert atmosphere; | 97% |
In ethanol; water at 70℃; for 1h; | 90% |
In methanol; water at 50℃; for 1h; | 89% |
aminoiminomethanesulfonic acid
1,2-diamino-benzene
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
In isopropyl alcohol at 60℃; | 95% |
formamide
1,2-diamino-benzene
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With N-sulfonated biguanidine modified silica coated on cobalt ferrite nanoparticle core In ethanol at 20℃; for 0.3h; Green chemistry; | 92% |
Conditions | Yield |
---|---|
In methanol; water at 20℃; for 24h; | 88% |
In water at 20℃; | 75% |
Conditions | Yield |
---|---|
at 700℃; under 0.02 Torr; Gas phase; | A 85% B 86% |
Conditions | Yield |
---|---|
at 700℃; under 0.02 Torr; Gas phase; | A 78% B 85% |
Conditions | Yield |
---|---|
Stage #1: bromocyane; o-phenylenediamine dihydrochloride With sodium hydrogencarbonate In water; acetonitrile at 0 - 20℃; Stage #2: With sodium carbonate In water; acetonitrile | 85% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 4h; Heating; | 82% |
N-tert-butyl-1H-benzo[d]imidazol-2-amine
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With hydrogenchloride In water for 12h; Reflux; | 82% |
1H-benzimidazol-2-ylcarbamic acid methyl ester
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With sodium hydroxide In water for 2h; Reflux; | 80% |
Stage #1: 1H-benzimidazol-2-ylcarbamic acid methyl ester With sodium hydroxide In water for 2h; Reflux; Stage #2: With hydrogenchloride In water | 65% |
With oxygen In various solvent(s) at 20℃; for 5h; pH=11; Quantum yield; Kinetics; Further Variations:; pH-values; Reagents; conc. of dissolved O2; Decomposition; Photolysis; | |
Alkaline conditions; | |
With water Alkaline conditions; |
N-(1H-benzimidazol-2-yl)-N'-benzylidenehydrazine
A
1H-benzimidazol-2-amine
B
benzonitrile
Conditions | Yield |
---|---|
at 700℃; under 0.02 Torr; Gas phase; | A 73% B 78% |
Conditions | Yield |
---|---|
Irradiation; microwave; | 75% |
Conditions | Yield |
---|---|
at 700℃; under 0.02 Torr; Gas phase; | A 65% B 67% |
Conditions | Yield |
---|---|
at 700℃; under 0.02 Torr; Gas phase; | A 65% B 10% C 58% |
1,3-dicarbethoxy-S-methylisothiourea
1,2-diamino-benzene
A
1H-benzimidazol-2-amine
B
1H-benzimidazol-2-ol
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 5h; Heating; | A 60% B 22% |
1,2-diamino-benzene
di(1H-imidazol-1-yl)methanimine
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
In tetrahydrofuran for 12h; Heating; | 59% |
N-cyano-N-phenyl-p-toluenesulfonamide
1,2-diamino-benzene
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 5 - 20℃; for 1h; Green chemistry; | 56% |
2-Amino-1-benzylideneaminobenzimidazole
A
1H-benzimidazol-2-amine
B
benzonitrile
Conditions | Yield |
---|---|
In nitrobenzene for 12h; Heating; | A 47% B n/a |
N-(1H-benzimidazol-2-yl)-N'-benzylidenehydrazine
A
1H-benzimidazol-2-amine
C
5,11-diphenyl-6H,12H-dibenzimidazo[1,2-a;1',2'-d]pyrazine
D
lophine
E
benzonitrile
Conditions | Yield |
---|---|
at 280℃; under 0.045 Torr; for 0.25h; Gas phase; | A 20% B 15% C 18% D 21% E 15% |
1H-benzimidazole-2-sulfonic acid
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With ammonium hydroxide at 145 - 150℃; for 5h; | |
With ammonium hydroxide | |
With ammonia |
Conditions | Yield |
---|---|
With formamide Heating; Yield given. Yields of byproduct given; | |
With formamide Heating; Yield given. Yields of byproduct given; | |
With formamide Product distribution; Heating; also 1-alkyl-substituted benzimidazole-2-sulfonic acids investigated; |
Conditions | Yield |
---|---|
With bromine 1) water, 5 deg C; 2) water, room temperature, 5 h.; Yield given. Multistep reaction; |
2-(1-ethylbenzimidazol-2-yl)methyleneaminobenzimidazole
A
1H-benzimidazol-2-amine
B
1-ethyl-1H-benzo[d]imidazole-2-carbaldehyde
Conditions | Yield |
---|---|
With water Hydrolysis; |
A
1H-benzimidazol-2-amine
B
1-vinylbenzimidazole-2-carboxaldehyde
Conditions | Yield |
---|---|
With water In dimethylsulfoxide-d6 for 120h; Hydrolysis; |
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With hydrogenchloride |
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With potassium hydroxide |
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With potassium hydroxide |
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
With hydrogenchloride |
1H-benzimidazol-2-amine
cyclohexanone-2-carboxamide
1,2,3,4,6,12-Hexahydrobenzimidazo<2,1-b>chinazolin-12-on
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 3h; Heating; | 100% |
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
In ethanol Reflux; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
Heating; | 99% |
With triethylamine for 16h; Cooling with ice; | 72% |
With triethylamine at 50 - 55℃; |
3-(2-furyl)-2-(2-methoxycarbonylphenylhydrazono)-3-oxo-propanal
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
In ethanol for 0.166667h; microwave irradiation; | 99% |
2-(2-methoxycarbonylphenylhydrazono)-3-oxo-3-(2-pyrrolyl)propanal
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
In ethanol for 0.166667h; microwave irradiation; | 99% |
1H-benzimidazol-2-amine
2-Hydroxy-1,4-naphthoquinone
4-nitrobenzaldehdye
2-(((1H-benzo[d]imidazol-2-yl)amino)(4-nitrophenyl)methyl)-3-hydroxynaphthalene-1,4-dione
Conditions | Yield |
---|---|
With MCM-41 In ethanol at 20℃; for 1.16667h; Green chemistry; | 99% |
With montmorillonite K-10 In ethanol at 20℃; for 8h; | 93% |
With indium(III) chloride In water for 6h; Reflux; | 80% |
1H-benzimidazol-2-amine
pyrimidine-2,4,5,6(1H,3H)-tetraone
2,5-dihydroxy-1,4-benzoquinone
2-amino-1H-benzo[d]imidazol-3-ium 3-hydroxy-1-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-2,5,6-trioxocyclohex-3-en-1-ide
Conditions | Yield |
---|---|
In chloroform for 4h; Reflux; | 99% |
1H-benzimidazol-2-amine
4-fluorobenzaldehyde
cyanoacetic acid amide
2,5-bis(4-fluorophenyl)-2,3,5,12-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrimido[4,5-d]pyrimidin-4(1H)-one
Conditions | Yield |
---|---|
With silica sulfuric acid In ethylene glycol at 120℃; for 0.0166667h; Catalytic behavior; Reagent/catalyst; Solvent; Green chemistry; | 99% |
With poly(ethylene glycol)-400 at 20℃; for 1h; Green chemistry; | 90% |
In water for 2h; Reflux; | 89% |
Conditions | Yield |
---|---|
With acetic acid at 60℃; for 0.333333h; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With silica sulfuric acid In ethylene glycol at 120℃; for 0.0166667h; Green chemistry; | 99% |
1H-benzimidazol-2-amine
2,3,5-trichloro-6-methoxybenzoic acid chloride
Conditions | Yield |
---|---|
With triethylamine In acetone at 55℃; | 98.7% |
98% |
1H-benzimidazol-2-amine
3-nitro-benzaldehyde
(1H-benzimidazol-2-yl)-(3-nitro-benzyliden)-amine
Conditions | Yield |
---|---|
In toluene for 20h; Heating; | 98% |
Conditions | Yield |
---|---|
With silica In acetonitrile at 25 - 30℃; for 0.5h; Green chemistry; | 98% |
With toluene-4-sulfonic acid In acetonitrile at 40 - 50℃; for 0.333333h; Green chemistry; | 98% |
With starch functionalized Fe3O4 nanoparticles In water at 20℃; for 0.116667h; Irradiation; Green chemistry; chemoselective reaction; | 98% |
Conditions | Yield |
---|---|
With starch functionalized Fe3O4 nanoparticles In water at 20℃; for 0.15h; Irradiation; Green chemistry; chemoselective reaction; | 98% |
With acetic acid at 60℃; for 0.333333h; Green chemistry; | 96% |
With 4-methyl-4-sulfonic acid morpholinium chloride at 90℃; for 0.0833333h; Reagent/catalyst; | 96% |
Conditions | Yield |
---|---|
In water for 0.025h; microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With butane-1-sulfonic acid modified starch coated γ-Fe2O3 magnetic nanoparticles In neat (no solvent) at 100℃; for 0.166667h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; | 98% |
With starch functionalized Fe3O4 nanoparticles In water at 20℃; for 0.116667h; Irradiation; Green chemistry; chemoselective reaction; | 98% |
With 4-methyl-4-sulfonic acid morpholinium chloride at 90℃; for 0.0666667h; Catalytic behavior; Reagent/catalyst; Temperature; | 97% |
3-(4-chlorophenyl)-2-(2-methoxycarbonylphenylhydrazono)-3-oxo-propanal
1H-benzimidazol-2-amine
Conditions | Yield |
---|---|
In ethanol for 0.166667h; microwave irradiation; | 98% |
1H-benzimidazol-2-amine
2-[hydroxy-(3-nitro-phenyl)-methyl]-acrylic acid methyl ester
6-[(3-nitrophenyl)hydroxymethyl]-5,6-dihydro-8H-benzo[4,5]imidazo[1,2-a]pyrimidin-7-one
Conditions | Yield |
---|---|
In 1,4-dioxane at 100℃; for 2h; | 98% |
In tetrahydrofuran; water at 50℃; for 24h; Michael addition-cyclization tandem reaction; | 77% |
pyridine-4-carbaldehyde
1H-benzimidazol-2-amine
ethyl acetoacetate
ethyl 2-methyl-4-(pyridin-4-yl)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylate
Conditions | Yield |
---|---|
With Thiamine hydrochloride In water for 3h; Reflux; | 98% |
With zinc perchlorate In methanol for 6h; Reflux; | 70% |
1H-benzimidazol-2-amine
ethyl acetoacetate
3-Chlorobenzaldehyde
4-(3-chlorophenyl)-2-methyl-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With poly(vinylpyrrolidonium) perchlorate ([PVPH]ClO4) at 100℃; for 0.333333h; | 98% |
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In neat (no solvent) at 100℃; for 0.666667h; Reagent/catalyst; Green chemistry; | 96% |
With 4,4'-(butane-1,4-diyl)bis(1-sulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium) tetrachloride In neat (no solvent) at 90℃; for 0.25h; Green chemistry; | 92% |
1H-benzimidazol-2-amine
2,5-bis(chloromethyl)-1,3,4-oxadiazole
C18H16N8O
Conditions | Yield |
---|---|
With potassium hydroxide In acetone Reflux; | 98% |
1H-benzimidazol-2-amine
4-ethoxy-1,1,1-trichloro-3-buten-2-one
2-(trichloromethyl)benzo[4,5]imidazol[1,2-a]pyrimidine
Conditions | Yield |
---|---|
With triethylamine In toluene for 2h; Reflux; | 98% |
1H-benzimidazol-2-amine
4-chlorobenzaldehyde
malononitrile
2-amino-4-(4-chlorophenyl)-1,4-dihydrobenzo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitrile
Conditions | Yield |
---|---|
With Ag-TiO2 nanocomposite In neat (no solvent) at 60℃; for 0.133333h; Catalytic behavior; Solvent; Temperature; | 98% |
With starch functionalized Fe3O4 nanoparticles In water at 20℃; for 0.05h; Irradiation; Green chemistry; chemoselective reaction; | 97% |
With poly(vinylpyrrolidonium) perchlorate ([PVPH]ClO4) at 100℃; for 0.25h; | 96% |
1H-benzimidazol-2-amine
4-fluorobenzaldehyde
malononitrile
2-amino-4-(4-fluorophenyl)-1,4-dihydrobenzo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitrile
Conditions | Yield |
---|---|
With starch functionalized Fe3O4 nanoparticles In water at 20℃; for 0.05h; Irradiation; Green chemistry; | 98% |
With Ag-TiO2 nanocomposite In neat (no solvent) at 60℃; for 0.133333h; | 97% |
With zinc ferrite In methanol at 70℃; for 1.48333h; Sonication; Green chemistry; | 92% |
1H-benzimidazol-2-amine
m-bromobenzoic aldehyde
malononitrile
2-amino-4-(3-bromophenyl)-1,4-dihydrobenzo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitrile
Conditions | Yield |
---|---|
With poly(vinylpyrrolidonium) perchlorate ([PVPH]ClO4) at 100℃; for 0.0666667h; | 98% |
With 1-methyl-3-(trimethoxysilylpropyl)imidazolium hydrogen sulfate supported on rice husk ash In neat (no solvent) at 100℃; for 0.05h; Green chemistry; | 90% |
With zinc ferrite In methanol at 70℃; for 1.36667h; Sonication; Green chemistry; | 90% |
1H-benzimidazol-2-amine
(4-isopropylbenzaldehyde)
malononitrile
2-amino-4-(4-isopropylphenyl)-1,4-dihydrobenzo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitrile
Conditions | Yield |
---|---|
With poly(vinylpyrrolidonium) perchlorate ([PVPH]ClO4) at 100℃; for 0.0666667h; | 98% |
With toluene-4-sulfonic acid In neat (no solvent) at 80℃; for 0.55h; Green chemistry; | 92% |
With 1-methyl-3-(trimethoxysilylpropyl)imidazolium hydrogen sulfate supported on rice husk ash In neat (no solvent) at 100℃; for 0.0833333h; Green chemistry; | 88% |
1H-benzimidazol-2-amine
4-bromo-benzaldehyde
malononitrile
2-amino-4-(4-bromophenyl)-1,4-dihydrobenzo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitrile
Conditions | Yield |
---|---|
With Ag-TiO2 nanocomposite In neat (no solvent) at 60℃; for 0.166667h; | 98% |
With starch functionalized Fe3O4 nanoparticles In water at 20℃; for 0.0666667h; Irradiation; Green chemistry; | 97% |
With poly(vinylpyrrolidonium) perchlorate ([PVPH]ClO4) at 100℃; for 0.333333h; | 95% |
1H-benzimidazol-2-amine
m-bromobenzoic aldehyde
ethyl acetoacetate
ethyl 4-(3-bromophenyl)-1,4-dihydro-2-methylpyrimido[1,2-a]benzimidazole-3-carboxylate
Conditions | Yield |
---|---|
With poly(vinylpyrrolidonium) perchlorate ([PVPH]ClO4) at 100℃; for 0.666667h; | 98% |
With Copper-polysulfonamide complex immobilized on graphene oxide In ethanol for 0.333333h; Reflux; | 95% |
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In neat (no solvent) at 100℃; for 0.583333h; Reagent/catalyst; Green chemistry; | 90% |
1H-benzimidazol-2-amine
3-[3-(2-oxiranyl-ethoxy)-6-oxo-6H-pyridazin-1-ylmethyl]-benzoic acid methyl ester
potassium 3-{3-[4-(2-amino-benzoimidazol-1-yl)-3-hydroxy-butoxy]-6-oxo-6H-pyridazin-1-ylmethyl}-benzoate
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 100℃; for 1h; Microwave irradiation; | 98% |
1. | mma-sat 710 µmol/L | ENMUDM Environmental Mutagenesis. 3 (1981),11. | ||
2. | mmo-sat 100 µg/plate | MUREAV Mutation Research. 15 (1972),273. | ||
3. | orl-rat TDLo:426 mg/kg (8-15D preg):TER | THERAP Therapie. 31 (1976),505. | ||
4. | orl-rat LDLo:500 mg/kg | NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),22. | ||
5. | orl-mus LD40:600 mg/kg | JACSAT Journal of the American Chemical Society. 67 (1945),905. | ||
6. | ipr-mus LD50:100 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . | ||
7. | ivn-mus LD50:126 mg/kg | 29QHAQ Principles of Medicinal Chemistry Foye, W.O., eds.,Philadelphia, PA.: Lea and Febiger,1974,246. |
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