Conditions | Yield |
---|---|
With sulfuric acid; nitric acid; sodium sulfate at 80℃; for 0.0363889h; Temperature; Microwave irradiation; | 90.5% |
With sulfuric acid; nitric acid In diethyl ether at 0 - 140℃; | 39% |
With sulfuric acid; nitric acid | |
With sulfuric acid; nitric acid; sodium sulfate In water at 130 - 132℃; for 4h; | |
With sulfuric acid; nitric acid; sodium sulfate at 150℃; for 2h; | 3.8 g |
2-methylimidazole
A
2-methyl-5-nitro-1H-imidazole
B
2-(dinitromethylene)-5,5-dinitro-4-imidazolidinone
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid for 3h; Nitration; |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid Nitration; | A 0.5 g B 4.5 g |
A
2-methyl-5-nitro-1H-imidazole
B
dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate Product distribution; Decomposition; |
2-methylimidazole
A
2-methyl-5-nitro-1H-imidazole
B
2-methyl-4-nitro-1H-imidazole
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In water at 130 - 132℃; for 4h; |
metronidazole
A
2-methyl-5-nitro-1H-imidazole
B
2-(5-amino-2-methyl-1H-imidazol-1-yl)ethan-1-ol
C
N-(2'-hydroxyethyl)-2-methylimidazole
Conditions | Yield |
---|---|
With sodium tetrahydroborate; iron at 25℃; pH=7; |
4-iodo-2-methyl-5-nitro-1H-imidazole
2-methyl-5-nitro-1H-imidazole
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; under 50 Torr; for 0.333333h; Pressure; | 89 %Chromat. |
4-bromo-2-methyl-5-nitroimidazole
2-methyl-5-nitro-1H-imidazole
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; under 100 Torr; for 0.5h; Pressure; | 47 %Chromat. |
2-methyl-5-nitro-1H-imidazole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; | 99.9% |
2-methyl-5-nitro-1H-imidazole
methanesulfonic acid 7-[tert-butoxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-6-{[tert-butoxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-methyl}-heptyl ester
(2-tert-butoxycarbonylamino-ethyl)-[2-{[tert-butoxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-methyl}-7-(2-methyl-4-nitro-imidazol-1-yl)-heptyl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 98% |
Conditions | Yield |
---|---|
Stage #1: 2-methyl-5-nitro-1H-imidazole With potassium carbonate In acetonitrile at 50℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In acetonitrile Reflux; | 95.6% |
Stage #1: 2-methyl-5-nitro-1H-imidazole With potassium carbonate In acetonitrile at 50℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In acetonitrile Reflux; |
2-methyl-5-nitro-1H-imidazole
acrylic acid methyl ester
methyl 3-(2-methyl-5-nitro-1H-imidazol-1-yl)propanoate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 168h; Michael Addition; Inert atmosphere; | 95.6% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 168h; Inert atmosphere; | 95.6% |
Conditions | Yield |
---|---|
for 50h; Heating; | 95% |
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide at 20℃; for 10h; aza-Markovnikov addition; | 95% |
2-methyl-5-nitro-1H-imidazole
Conditions | Yield |
---|---|
Stage #1: 2-methyl-5-nitro-1H-imidazole With potassium carbonate In acetonitrile Heating; Stage #2: 2-phenyl-3-((3-bromopropoxy)methyl)-imidazo[2,1-b] benzothiazole In acetonitrile Heating; | 94.6% |
2-methyl-5-nitro-1H-imidazole
Conditions | Yield |
---|---|
Stage #1: 2-methyl-5-nitro-1H-imidazole With potassium carbonate In acetonitrile at 60℃; for 1h; Stage #2: 2-phenyl-3-((3-bromopropoxy)methyl)-imidazo[2,1-b] benzothiazole In acetonitrile at 60℃; | 94.2% |
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide at 20℃; for 30h; aza-Markovnikov addition; | 94% |
3-chloropropiophenone
2-methyl-5-nitro-1H-imidazole
3-(2-methyl-5-nitro-1H-imidazol-1-yl)-1-phenylpropan-1-one
Conditions | Yield |
---|---|
With triethylamine In toluene at 20℃; Reflux; | 94% |
Conditions | Yield |
---|---|
With potassium phosphate In N,N-dimethyl-formamide at 50℃; for 30h; aza-Markovnikov addition; | 93% |
2-methyl-5-nitro-1H-imidazole
4-bromo-2-methyl-5-nitroimidazole
Conditions | Yield |
---|---|
With bromine; sodium carbonate In N,N-dimethyl-formamide at 70℃; for 2h; | 93% |
With bromine In N,N-dimethyl-formamide at 40℃; for 4h; Cooling with ice; | 75% |
2-methyl-5-nitro-1H-imidazole
1-phenyl-2-bromoethane
2-methyl-4-nitro-1-phenethyl-1H-imidazole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 8h; Schlenk technique; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
Stage #1: 2-methyl-5-nitro-1H-imidazole With potassium carbonate In acetonitrile at 60℃; for 1h; Stage #2: C21H21BrN2O2S In acetonitrile at 60℃; | 93% |
2-methyl-5-nitro-1H-imidazole
methanesulfonic acid 6,6-bis-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-hexyl ester
{2-[2-(2-tert-butoxycarbonylamino-ethylcarbamoyl)-7-(2-methyl-4-nitro-imidazol-1-yl)-heptanoylamino]-ethyl}-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 92% |
Conditions | Yield |
---|---|
Stage #1: 2-methyl-5-nitro-1H-imidazole With potassium carbonate In acetonitrile at 60℃; for 1h; Stage #2: C21H21BrN2OS In acetonitrile at 60℃; | 92% |
Conditions | Yield |
---|---|
Stage #1: 2-methyl-5-nitro-1H-imidazole With potassium carbonate In acetonitrile at 60℃; for 1h; Stage #2: C23H25BrN2O2S In acetonitrile at 60℃; | 91% |
2-methyl-5-nitro-1H-imidazole
acrylonitrile
3-(2-methyl-4-nitro-1H-imidazol-1-yl)propanenitrile
Conditions | Yield |
---|---|
With potassium carbonate Reflux; | 90% |
With polystyrene-supported CuI-imidazole complex catalyst In N,N-dimethyl-formamide at 100℃; for 10h; Aza-Michael reaction; | 77% |
Conditions | Yield |
---|---|
With silica gel In neat (no solvent) at 100℃; for 4.5h; | 90% |
ethyl 1-(oxiran-2-ylmethyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate
2-methyl-5-nitro-1H-imidazole
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 60℃; for 1.5h; | 89.3% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 70℃; for 5h; Reagent/catalyst; Temperature; | 89.1% |
2-methyl-5-nitro-1H-imidazole
propargyl bromide
A
N1-propargyl-2-methyl-4-nitroimidazole
B
2‐methyl‐5‐nitro‐1‐prop‐2‐ynyl‐1H‐imidazole
Conditions | Yield |
---|---|
With potassium carbonate In acetone; toluene at 20℃; Inert atmosphere; | A n/a B 89% |
2-methyl-5-nitro-1H-imidazole
phenoxyethyl bromide
2-methyl-4-nitro-1-(2-phenoxyethyl)-1H-imidazole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 8h; Schlenk technique; Inert atmosphere; | 89% |
ethyl 6-methyl-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
2-methyl-5-nitro-1H-imidazole
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 60℃; for 1.5h; | 88.4% |
(S)-epichlorohydrin
2-methyl-5-nitro-1H-imidazole
(S)-(-)-1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole
Conditions | Yield |
---|---|
With aluminum (III) chloride In ethyl acetate at 3 - 5℃; | 88.2% |
With formic acid; sulfuric acid at 30 - 40℃; for 4.5h; Reagent/catalyst; Temperature; | 83.9% |
With formic acid; sulfuric acid at -5 - 15℃; for 2h; Reagent/catalyst; | 403 g |
With boron trifluoride In ethyl acetate at -10 - 15℃; for 5h; Darkness; Large scale; | 3.21 kg |
With boron trifluoride In ethyl acetate at -10 - 15℃; for 5h; Darkness; Large scale; | 3.21 kg |
Conditions | Yield |
---|---|
With formic acid; sulfuric acid at 80℃; for 12h; Temperature; | 88% |
With formic acid at 50 - 60℃; for 0.5h; Reagent/catalyst; Temperature; | 74.9% |
With phosphoric acid; acetic anhydride In water at 25 - 30℃; for 2.5h; Yield given; | |
With sulfuric acid; acetic acid at 90℃; for 0.5h; Concentration; Temperature; Cooling; | |
With formic acid; sulfuric acid Large scale; |
1-bromo-butane
2-methyl-5-nitro-1H-imidazole
1-butyl-2-methyl-4-nitro-1H-imidazole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 8h; Schlenk technique; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With formic acid for 4h; Reflux; | 87% |
Conditions | Yield |
---|---|
Stage #1: 2-methyl-5-nitro-1H-imidazole With potassium carbonate In acetonitrile at 60℃; for 1h; Stage #2: C26H31BrN2OS In acetonitrile at 60℃; | 87% |
1. | mmo-sat 3 mmol/L | MUREAV Mutation Research. 66 (1979),207. | ||
2. | mmo-klp 5 mmol/L/20H | MUREAV Mutation Research. 66 (1979),207. |
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