[ CAS No. 18994-90-6 ]

Name: 18994-90-6|1-(4-Nitrobenzyl)-1H-imidazole(Chunks or pellets)|98% (contains <10%H2O)
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CAS No. :	18994-90-6	MDL No. :	MFCD01799096
Formula :	C₁₀H₉N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FLYGQJXMRPZYHQ-UHFFFAOYSA-N
M.W :	203.20	Pubchem ID :	585819
Synonyms :

Safety of [ 18994-90-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P273-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335-H412	Packing Group:	N/A
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* 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.

Upstream synthesis route of [ 18994-90-6 ]
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[ 18994-90-6 ] Synthesis Path-Upstream 1~2

1
[ 693-98-1 ]
[ 18994-90-6 ]
[ 56643-86-8 ]

Reference： [1] Patent: US6048884, 2000, A,

2
[ 18994-90-6 ]
[ 56643-85-7 ]

Reference： [1] Farmaco, Edizione Scientifica, 1986, vol. 41, # 4, p. 292 - 307
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 4, p. 1712 - 1725
[3] Journal of Medicinal Chemistry, 1990, vol. 33, # 5, p. 1312 - 1329
[4] Patent: US2008/81802, 2008, A1, . Location in patent: Page/Page column 11
[5] Patent: US2010/81653, 2010, A1, . Location in patent: Page/Page column 13
[6] Patent: WO2011/46970, 2011, A1, . Location in patent: Page/Page column 163
[7] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5505 - 5512

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Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In acetonitrile for 15h; Irradiation;
90%	With potassium carbonate In acetonitrile Reflux;	5.2. General procedure 1 General procedure: Compounds 1-18 were synthesized using the following generalprocedure reported by Salvio et al. [41]. A mixture of potassium carbonate(2.0 g, 14.4 mmol), imidazole derivatives 27-28 (32.9 mmol)and compounds 29-37 (4.7 mmol) in dry acetonitrile (50 ml) was heatedunder reflux and the progress of the reaction was monitored byTLC. Then the solvent was evaporated under the vacuum and the residuewas dissolved in DCM (100 ml) . The organic layer was washedwith saturated sodium bicarbonate aqueous solution (2×50 ml),passed through diatomaceous earth, dried over sodium sulfate, evaporatedunder the vacuum, and purified by flash column chromatography(ethyl acetate-hexane 0-100%)* to give the products 1-18.Note 1: Ethyl acetate (200 ml) was used for compounds 17 and 18.*Note 2: Compounds 17 and 18 (ethyl acetate-methanol 0-100%).
	With potassium carbonate In acetonitrile Varying the time. Reaction in the dark and under light (lamp), in the absence and presence of para-dinitrobenzene or tetramethyl-4,4,6,6-piperidine nitroxyde;

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate In acetonitrile at 20℃; for 12h;
94%	With potassium carbonate In N,N-dimethyl-formamide at 200℃; for 0.25h; Microwave irradiation;	General procedure for 1-(4-nitrobenzyl)-1H-imidazole (1) 4-Nitrobenzyl (6.13 g, 0.04 mol), K2CO3 (5.52 g, 0.04 mol),1H-imidazole (2.72 g, 0.04 mol), and DMF (10 mL) wereadded into a vial (30 mL) of microwave synthesis reactor(Anton-Paar Monowave 300). The reaction mixture, washeated under conditions of 200 °C and 10 bar for 15 min.After cooling, the mixture was poured into iced-water, precipitatedproduct was washed with water, dried and recrystallizedfrom ethanol. Yield: 94%; m.p. 49 C. Literaturem.p. 48-51 °C. [31]
91%	With potassium carbonate In acetonitrile	8.1 A. Step 1. 4-(1-Imidazolylmethyl)-1-nitrobenzene To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO3 (1.0 g, 7.3 mmol). The resulting mixture was stirred at room temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution was extracted with EtOAc (350 mL). The combined organic layers were sequentially washed with water (350 mL) and a saturated NaCl solution (2*50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91%): El-MS m/z 203 (M+).

91%	With potassium carbonate In ethyl acetate; acetonitrile	1 4-(1-Imidazolylmethyl)-1-nitrobenzene Step 1. 4-(1-Imidazolylmethyl)-1-nitrobenzene To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO3 (1.0 g, 7.3 mmol). The resulting mixture was stirred at rooom temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution wasextracted with EtOAc (350 mL). The combined organic layers were sequentially washed with water (350 mL) and a saturated NaCl solution (2*50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91%): El-MS m/z 203 (M+).
91%	With potassium carbonate In acetonitrile at 20℃; for 18h;	A.18.1 Step 1. 4-(1-Imidazolylmethyl)-1-nitrobenzene To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO (1.0 g, 7.3 mmol). The resulting mixture was stirred at room temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution was extracted with EtOAc (350 mL). The combined organic layers were sequentially washed with water (350 mL) and a saturated NaCl solution (2*50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91%): EI-MS m/z 203 (M+).
91%	With potassium carbonate In acetonitrile at 20℃; for 18h;	A.A18.1 A. General Methods for Synthesis of Substituted Anilines A18. General Method for Synthesis of Aryl Amines via Substitution with Nitrobenzyl Halides Followed by Reduction Step 1. 4-(1-Imidazolylmethyl)-1-nitrobenzene To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO3 (1.0 g, 7.3 mmol). The resulting mixture was stirred at rooom temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution wasextracted with EtOAc (3 x 50 mL). The combined organic layers were sequentially washed with water (3 x 50 mL) and a saturated NaCl solution (2 x 50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91 %): EI-MS m/z 203 (M+).
91%	With potassium carbonate In acetonitrile at 20℃; for 18h;	A18.1 A18. General Method for Synthesis of Aryl Amines via Substitution with Nitrobenzyl Halides Followed by Reduction; [] Step 1. 4-(1-Imidazolylmethyl)-1-nitrobenzene: To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO3 (1.0 g, 7.3 mmol). The resulting mixture was stirred at rooom temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution wasextracted with EtOAc (3 x 50 mL). The combined organic layers were sequentially washed with water (3 x 50 mL) and a saturated NaCl solution (2 x 50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91%): EI-MS m/z 203 (M+).
91%	With potassium carbonate In acetonitrile at 20℃; for 18h;	B.B8.1 B8. General Method for Synthesis of Aryl Amines Via Substitution with Nitrobenzyl Halides Followed by Reduction; Step 1. 4-(1-Imidazolylmethyl)-1-nitrobenzene; To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO3 (1.0 g, 7.3 mmol). The resulting mixture was stirred at room temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution was extracted with EtOAc (3×50 mL). The combined organic layers were sequentially washed with water (3×50 mL) and a saturated NaCl solution (2×50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91%): EI-MS m/z 203 (MO).
91%	With potassium carbonate In acetonitrile at 20℃; for 18h;	A.A8.1 Step 1. 4-(1-Imidazolylmethyl)-1-nitrobenzene To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO3 (1.0 g, 7.3 mmol). The resulting mixture was stirred at room temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution was extracted with EtOAc (350 mL). The combined organic layers were sequentially washed with water (350 mL) and a saturated NaCl solution (2*50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91%): EI-MS m/z 203 (M+).
91%	With potassium carbonate In acetonitrile at 20℃; for 18h;	B8.1 Step 1. 4-(1-Imidazolylmethyl)-1-nitrobenzene To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO3 (1.0 g, 7.3 mmol). The resulting mixture was stirred at room temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution was extracted with EtOAc (350 mL). The combined organic layers were sequentially washed with water (350 mL) and a saturated NaCl solution (2*50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91%): EI-MS m/z 203 (M+).
91%	With potassium carbonate In acetonitrile at 20℃; for 18h;	B.1 To a solution of imidazole (0.5 g, 7.3 mmol) and 4-nitrobenzyl bromide (1.6 g, 7.3 mmol) in anh acetonitrile (30 mL) was added K2CO3 (1.0 g, 7.3 mmol). The resulting mixture was stirred at rooom temp. for 18 h and then poured into water (200 mL) and the resulting aqueous solution wasextracted with EtOAc (3 x 50 mL). The combined organic layers were sequentially washed with water (3 x 50 mL) and a saturated NaCl solution (2 x 50 mL), dried (MgSO4), and concentrated in vacuo. The residual oil was purified by MPLC (silica gel; 25% EtOAc/75% hexane) to afford the desired product (1.0 g, 91 %): EI-MS m/z 203 (M+).
85%	With sodium carbonate In chloroform for 3h;
85%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h;	503.1 l-(Bromomethyl)-4-nitro-benzene (1.0 g, 4.6 mmol) was dissolved in DMF (2.0 mL) and added to a solution of imidazole (1.89 g, 27.7 mmol) and DIPEA (0.90 mL, 5.09 mmol) in DMF (10 mL). The reaction mixture was stirred for 16 h. The solvent was removed and H20 and EtOAc were added. The organic layer was separated, dried over sodium sulfated and the solvent evaporated. Purification by column chromatograpy afforded the title compound (0.8 g, 85%). 1H NMR (DMSO- 6) δ 8.23 (dt, 2H), 7.80 (d, 1H), 7.46 (dt, 2H), 7.23 (t, 1H), 6.95 (t, 1H), 5.39 (s, 1H).
53%	Stage #1: 1H-imidazole With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1-bromomethyl-4-nitro-benzene In N,N-dimethyl-formamide at 50℃; for 24h;
42%	With potassium carbonate In acetone Reflux;
18%	In N,N-dimethyl-formamide at 25℃; for 16h;
	With sodium methylate 1.) methanol, 0 deg C, 2.) DMF, 25 deg C; Multistep reaction;
	With potassium carbonate In tetrahydrofuran Heating;
	With potassium carbonate at 20℃;	Potassium carbonate (3.1 g, 23 mmol) is added to a solution of 4-nitrobenzylbromide (5 g, 23 mmol) and imidazole (1.6 g, 23 mmol) and the reaction mixture is stirred at RT. After the reaction has been completed according to HPLC-MS the suspension is poured into 800 mL water and extracted three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried on sodium sulphate and evaporated down. The residue is purified by chromatography on silica gel with dichloromethane/methanol. Yield: 2.1 g.
	With potassium carbonate In acetonitrile at 20℃; for 17h;	13 Potassium carbonate (2.00 g; 14.6 mmol) was added to a stirred solution of 1-(bromomethyl)-4-nitrobenzene (3.20 g; 14.8 mmol) and imidazole (1.00 g; 14.7 mmol) in acetonitrile (60 mL). The mixture was stirred at room temperature for 17 hr and then concentrated under reduced pressure. The residue was partitioned between EA and water and the phases separated. The aqueous phase was extracted twice with EA; and the combined organic layers washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 1-(4-nitrobenzyl)-1H-imidazole (1.27 g) as a red/brown oil. A solution of 1-(4-nitrobenzyl)-1H-imidazole (2.67 g; 13.1 mmol) in ethanol (100 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (0.285 g) at room temperature for 4.5 hr. The mixture was filtered through diatomaceous earth and then concentrated under reduced pressure to give 4-[(1H-imidazol-1-ylmethyl]benzenamine (2.24 g) as a white solid.
	With potassium carbonate In acetonitrile for 5h; Reflux;

Yield	Reaction Conditions	Operation in experiment
67%	With hydrogenchloride; zinc; In ethanol; water; for 1h;Reflux;	1-(4-nitrobenzyl)-1H-imidazole (1) (7.11 g, 0.035 mol) wasdissolved in ethanol (100 mL) and 25% HCl (100 mL) mixture.Zinc powder (39.49 g, 0.35 mol) was divided into tenequal portions and each portion was added to the stirringsolution in 15 min intervals. Once the addition of the zincwas completed, reaction mixture was refluxed for 1 h. Hotsolution was allowed to cool down, poured into ice waterand then neutralized by using 10% NaOH solution. The precipitatewas extracted with ethyl acetate (3100 mL). The extracts were combined and filtered over anhydrous Na2SO4.The solvent was evaporated and the residue was recrystallized from ethanol to give the 1-(4-aminobenzyl)-1H-imidazole(2). Yield: 67%; m.p. 126 C. Literature m.p. 127 C.[32]
	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; ethyl acetate; at 20℃; under 2550.26 Torr;	A solution of H-5a (2.1 g, 10 mmol) in 10 mL ethanol, 10 mL ethyl acetate and 13 mL 1 M hydrochloric acid is combined with palladium (10% on activated charcoal, 0.27 g) in a hydrogenation reactor and stirred overnight at RT under 3.4 bar hydrogen pressure. The reaction mixture is filtered, evaporated down and codistilled three times with ethanol. Yield: 1.8 g.
	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 760.051 Torr; for 4.5h;	Potassium carbonate (2.00 g; 14.6 mmol) was added to a stirred solution of 1-(bromomethyl)-4-nitrobenzene (3.20 g; 14.8 mmol) and imidazole (1.00 g; 14.7 mmol) in acetonitrile (60 mL). The mixture was stirred at room temperature for 17 hr and then concentrated under reduced pressure. The residue was partitioned between EA and water and the phases separated. The aqueous phase was extracted twice with EA; and the combined organic layers washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 1-(4-nitrobenzyl)-1H-imidazole (1.27 g) as a red/brown oil. A solution of 1-(4-nitrobenzyl)-1H-imidazole (2.67 g; 13.1 mmol) in ethanol (100 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (0.285 g) at room temperature for 4.5 hr. The mixture was filtered through diatomaceous earth and then concentrated under reduced pressure to give 4-[(1H-imidazol-1-ylmethyl]benzenamine (2.24 g) as a white solid.

[ CAS No. 18994-90-6 ]

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[ 18994-90-6 ] Synthesis Path-Upstream 1~2

[ 18994-90-6 ] Synthesis Path-Downstream 1~52