144689-94-1

Basic information

• Product Name: Diethyl 2-propylImidazoledicarbonate
• Synonyms: 2-PROPYL-1H-IMIDAZOLE-4,5-DICARBOXYL;2-Propylimidazoledicarboxylic acid diethyl ester;2-PROPYL-4,5-IMIDAZOLEDICARBOXYLIC ACID DIETHYL ESTER 98.0%;2-propyl-, diethyl ester;1H-Imidazole-4,5-dicarboxylic acid, 2-propyl-, 4,5-diethyl ester;2-proyl-4,5-imidazoledicarboxylic acid diethyl ester;4,5-diethyl 2-propyl-1H-iMidazole-4,5-dicarboxylate;2-Propyl-1H-iMidazole-4,5-dicarboxylic Acid 4,5-Diethyl Ester
• CAS NO: 144689-94-1
• Molecular Formula: C₁₂H₁₈N₂O₄
• Molecular Weight: 254.28
• EINECS: 1592732-453-0
• Product Categories: Pharmaceutical material and intermeidates;Organic acids;Aromatics;Intermediates
• Mol File: 144689-94-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 86 °C
• Boiling Point: 400.9 °C at 760 mmHg
• Flash Point: 196.2 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.25±0.10(Predicted)
• CAS DataBase Reference: Diethyl 2-propylImidazoledicarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 2-propylImidazoledicarbonate(144689-94-1)
• EPA Substance Registry System: Diethyl 2-propylImidazoledicarbonate(144689-94-1)

Safety Data

• Hazardous Substances Data: 144689-94-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 144689-94-1 differently. You can refer to the following data:
1. Diethyl 2-propylImidazoledicarbonate is an intermediate in the synthesis of Olmesartan Medoxomil.
2. An intermediate in the synthesis of Olmesartan Medoxomil. (O550000)

Chemical Properties

Light Yellow Solid

InChI:InChI=1/C12H18N2O4/c1-4-7-8-13-9(11(15)17-5-2)10(14-8)12(16)18-6-3/h4-7H2,1-3H3,(H,13,14)

Synthetic route

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + ethanol (64-17-5) → 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1)

Conditions	Yield
Stage #1: 2-propyl-1H-imidazole-4,5-dicarboxylic acid; ethanol With hydrogenchloride; thionyl chloride at 5℃; for 0.166667h; Stage #2: for 1.5h; Heating;	94%
With hydrogenchloride Ambient temperature;	86%
With thionyl chloride In water at 8℃; for 6.6h; Temperature; Reflux;	77%
at 0℃; for 12h; Reflux;

diethyl 2,3-dioxosuccinate (59743-08-7) + butyraldehyde (123-72-8) → 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1)

Conditions	Yield
With ammonia In tetrahydrofuran at 30 - 70℃; for 6h;	85.5%
With ammonium acetate In tetrahydrofuran; acetic acid at 60℃; for 3h; Product distribution / selectivity; light-shielding conditions;

butylamidine hydrochloride (3020-81-3) + diethyl 3-chloro-2-oxosuccinate (34034-87-2) → 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1)

Conditions	Yield
With pyridine In propan-1-ol for 6h; Reagent/catalyst; Solvent; Reflux;	80%

2-propylimidazole-4,5-dicarbonitrile (51802-42-7) → 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / 6N aq. HCl / 8 h / Heating 2: 86 percent / HCl / Ambient temperature View Scheme

diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate hydrochloride → 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1)

Conditions	Yield
With sodium chloride; sodium hydroxide In water for 1h; Cooling with ice;

methyl bromide (74-83-9) + 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate (144689-93-0)

Conditions	Yield
With iodine; magnesium In dichloromethane at 15 - 25℃; for 2h;	97.5%

methylmagnesium bromide (75-16-1) + 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate (144689-93-0)

Conditions	Yield
In diethyl ether; dichloromethane at 10 - 15℃; for 1h;	95%

methylmagnesium chloride (676-58-4) + 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate (144689-93-0)

Conditions	Yield
Stage #1: methylmagnesium chloride; diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran at -10 - 0℃; for 0.166667h; Stage #2: With water; ammonium chloride In tetrahydrofuran; dichloromethane	85%
Stage #1: methylmagnesium chloride; diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran; toluene for 6.5h; Inert atmosphere; Cooling with ice; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene pH=7;
In tetrahydrofuran at 60℃; for 2h;	4.81 g

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 50℃; for 4h;	85%

ethylmagnesium bromide (925-90-6) + 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 5-(1-Ethyl-1-hydroxy-propyl)-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (172875-50-2)

Conditions	Yield
In diethyl ether; dichloromethane at 10 - 15℃; for 1h;	83%

methylene chloride (74-87-3) + 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate (144689-93-0)

Conditions	Yield
Stage #1: methylene chloride With magnesium In tetrahydrofuran for 0.5h; Reflux; Stage #2: diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate In tetrahydrofuran at 30℃; for 2.5h; Solvent; Temperature;	80%
Stage #1: methylene chloride With magnesium at 55 - 60℃; for 1h; Inert atmosphere; Stage #2: diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate at 0℃; for 8h;

4'-bromomethyl-biphenyl-2-carboxylic acid tert-butyl ester (114772-40-6) + 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → diethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-propylimidazole-4,5-dicarboxylate (144690-85-7)

Conditions	Yield
With potassium tert-butylate 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h; Yield given. Multistep reaction;

N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole (133051-88-4) + 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 2-Propyl-1-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazole-4,5-dicarboxylic acid diethyl ester (172875-56-8)

Conditions	Yield
With potassium tert-butylate 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h; Yield given. Multistep reaction;

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → ethyl 4-isopropenyl-2-propylimidazole-5-carboxylate (157356-73-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → ethyl 4-isopropyl-2-propylimidazole-5-carboxylate (172875-51-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h 3: 93 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-methyl-2-propyl-3H-imidazole-4-carboxylic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 82 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 20 h / -5 °C 3: 100 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature 4: 61 percent / Bu3SnH, 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Heating 5: 89 percent / HCl / dioxane / 16 h / Ambient temperature 6: 94 percent / NaOH / dioxane; H2O / 5 h / 70 °C View Scheme
Multi-step reaction with 6 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: LiAlH(O-t-Bu)3 / tetrahydrofuran / 120 h / Ambient temperature 3: 100 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature 4: 61 percent / Bu3SnH, 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Heating 5: 89 percent / HCl / dioxane / 16 h / Ambient temperature 6: 94 percent / NaOH / dioxane; H2O / 5 h / 70 °C View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropyl-2-propyl-3H-imidazole-4-carboxylic acid

Conditions

Yield

Multi-step reaction with 6 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h 3: 93 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature 4: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 5: 82 percent / HCl / dioxane / 16 h / Ambient temperature 6: 100 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropenyl-2-propyl-3H-imidazole-4-carboxylic acid

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h 3: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 4: 92 percent / HCl / dioxane / 16 h / Ambient temperature 5: 94 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → ethyl 1-<(2'-carboxybiphenyl-4-yl)methyl>-4-methyl-2-propylimidazole-5-carboxylate (172876-10-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 82 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 20 h / -5 °C 3: 100 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature 4: 61 percent / Bu3SnH, 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Heating 5: 89 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: LiAlH(O-t-Bu)3 / tetrahydrofuran / 120 h / Ambient temperature 3: 100 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature 4: 61 percent / Bu3SnH, 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Heating 5: 89 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 1-(2'-Carboxy-biphenyl-4-ylmethyl)-5-hydroxymethyl-2-propyl-1H-imidazole-4-carboxylic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 66 percent / LiAlH(O-t-Bu)3 / tetrahydrofuran / 120 h / Ambient temperature 3: 100 percent / HCl / dioxane / 16 h / Ambient temperature 4: 100 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-hydroxymethyl-2-propyl-3H-imidazole-4-carboxylic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 82 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 20 h / -5 °C 3: 93 percent / HCl / dioxane / 16 h / Ambient temperature 4: 96 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: LiAlH(O-t-Bu)3 / tetrahydrofuran / 120 h / Ambient temperature 3: 93 percent / HCl / dioxane / 16 h / Ambient temperature 4: 96 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 1-[(2’-carboxybiphenyl-4-yl)methyl]-2-propylimidazole-4,5-dicarboxylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 96 percent / HCl / dioxane / 16 h / Ambient temperature 3: 100 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 4'-(4,5-Bis-hydroxymethyl-2-propyl-imidazol-1-ylmethyl)-biphenyl-2-carboxylic acid tert-butyl ester (154237-82-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 66 percent / LiAlH(O-t-Bu)3 / tetrahydrofuran / 120 h / Ambient temperature 3: 77 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 20 h / -5 °C View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropyl-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (172875-76-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h 3: 93 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature 4: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 5: 82 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-isopropenyl-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (172875-80-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h 3: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 4: 92 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-hydroxymethyl-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (154237-91-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 82 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 20 h / -5 °C 3: 93 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: LiAlH(O-t-Bu)3 / tetrahydrofuran / 120 h / Ambient temperature 3: 93 percent / HCl / dioxane / 16 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 5-Methyl-2-propyl-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 69 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 20 h / -5 °C 3: Et3N / CH2Cl2 / 0.5 h / Ambient temperature 4: 87 percent / Bu3SnH, 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Heating 5: 96 percent / 25percent aq. AcOH / 2.5 h / 80 °C 6: 97 percent / NaOH / dioxane; H2O / 5 h / 70 °C View Scheme
Multi-step reaction with 6 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: LiAlH(O-t-Bu)3 / tetrahydrofuran / 192 h 3: Et3N / CH2Cl2 / 0.5 h / Ambient temperature 4: 87 percent / Bu3SnH, 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Heating 5: 96 percent / 25percent aq. AcOH / 2.5 h / 80 °C 6: 97 percent / NaOH / dioxane; H2O / 5 h / 70 °C View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 1-[(2'-carboxybiphenyl-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 3: 92 percent / HCl / dioxane / 16 h / Ambient temperature 4: 91 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-tert-Butoxycarbonyl-biphenyl-4-ylmethyl)-5-methyl-2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (172876-05-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: 82 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 20 h / -5 °C 3: 100 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature 4: 61 percent / Bu3SnH, 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 2: LiAlH(O-t-Bu)3 / tetrahydrofuran / 120 h / Ambient temperature 3: 100 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature 4: 61 percent / Bu3SnH, 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Heating View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → XF 818

Conditions

Yield

Multi-step reaction with 6 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h 3: 93 percent / H2 / 10percent Pd/C / methanol / 3 h / Ambient temperature 4: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 5: 93 percent / 25percent aq. AcOH / 2.5 h / 80 °C 6: 89 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 1-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-4-(prop-1-en-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) POCl3, 2.) pyridine / 1.) benzene, reflux, 1 h, 2.) benzene, reflux, 1 h 3: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 4: 94 percent / 25percent aq. AcOH / 2.5 h / 80 °C 5: 85 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 3-(2'-Carboxy-biphenyl-4-ylmethyl)-5-(1-ethyl-1-hydroxy-propyl)-2-propyl-3H-imidazole-4-carboxylic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 83 percent / diethyl ether; CH2Cl2 / 1 h / 10 - 15 °C 2: 1.) t-BuOK / 1.) DMA, 0 deg C, 10 min, 2.) DMA, RT, 1 h 3: 92 percent / HCl / dioxane / 16 h / Ambient temperature 4: 95 percent / LiOH*H2O / dioxane; H2O / 5 h / Ambient temperature View Scheme

Upstream product

• 58954-23-7 2-propyl-1H-imidazole-4,5-dicarboxylic acid 
• 64-17-5 ethanol 
• 51802-42-7 2-propylimidazole-4,5-dicarbonitrile 
• 3020-81-3 butylamidine hydrochloride 
• 34034-87-2 diethyl 3-chloro-2-oxosuccinate 
• 59743-08-7 diethyl 2,3-dioxosuccinate 
• 123-72-8 butyraldehyde 

Downstream Products

• 144690-85-7 diethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-propylimidazole-4,5-dicarboxylate 
• 172875-56-8 2-Propyl-1-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazole-4,5-dicarboxylic acid diethyl ester 
• 144689-93-0 ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate 
• 144690-96-0 1-[{2'-cyanobiphenyl-4-yl}methyl]-4-(1-hydroxy-1-methylethyl)-2-propylimidazol-5-carboxylic acid ethyl ester 
• 1199807-37-8 diethyl 1-(2'-cyanobiphenyl-4-yl)methyl-2-propyl-1H-imidazole-4,5-dicarboxylate 
• 172875-53-5 ethyl 4-(1-hydroxy-1-methylpropyl)-2-propylimidazole-5-carboxylate 
• 1378863-72-9 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylpropyl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate 
• 1378863-74-1 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylpropyl)-2-propyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]imidazole-5-carboxylate 
• 1378863-69-4 ethyl 4-(1-hydroxy-1-methylpropyl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylate 
• 58954-23-7 2-propyl-1H-imidazole-4,5-dicarboxylic acid 
• 1020157-01-0 (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2′-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate 
• 1027174-22-6 5-(1-Hydroxy-1-methyl-ethyl)-2-propyl-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester 
• 172876-04-9 5-Hydroxymethyl-2-propyl-1-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazole-4-carboxylic acid ethyl ester 
• 172875-70-6 5-Isopropenyl-2-propyl-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid ethyl ester 

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Preparation method of 2-propyl-4, 5-imidazole diethyl dicarboxylate

The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of 2-propyl-4, 5-imidazole diethyl dicarboxylate, which comprises the following steps: by using L-tartaric acid as an initial raw material, carrying out esterification reaction, oxidation reaction and cyclization reaction to obtain the 2-propyl-4, 5-imidazole diethyl dicarboxylate product. A one-pot method is adopted for preparation, the method is simple, safety is good, and industrial production is easy to implement; the method has the advantages of mild reaction conditions, less three wastes, simple distillation and recycling of the solvent, simple process, low cost, high product purity and high yield compared with the existing process.

2-aminoalkylimidazole -4, 5-dicarboxilic manufacturing method

PROBLEM TO BE SOLVED: To provide a method for producing inexpensively with a high yield, 2-alkylimidazole-4,5-dicarboxylic acid which is useful as a medicinal intermediate. SOLUTION: In this method for producing 2-alkylimidazole-4,5-dicarboxylic acid, tartaric acid is dissolved into nitric acid and then reacted with concentrated sulfuric acid, and a nitrate of tartaric acid acquired by the reaction is added into a solvent containing at least one kind of organic solvent selected from among N-methyl-2-pyrrolidone, dimethylformamide, dimethylacetamide, methylcyclohexane and toluene. Thereafter, a mixed liquid of aldehyde and ammonia is added to the reaction liquid, to thereby produce 2-alkylimidazole-4,5-dicarboxylic acid. COPYRIGHT: (C)2012,JPOandINPIT