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Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Structure
CAS No.
144689-93-0
Chemical Name:
Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate
Synonyms
4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-1H-IMIDAZOLE-5-CARBOXYLIC ACID ETHYL ESTER;ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-iMidazole-5-carboxylate;ETHYL-4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-IMIDAZOLE-5-CARBOXYLATE;Olmesartan intermediate;4-(1-Hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid;5-(1-HYDROXYL-1-METHYLETHYL)-2-PROPYL-IMIDAZOL-4-YLCARBOXYLIC ACID ETHYL ESTER;1H-Imidazole-5-carboxylic acid, 4-(1-hydroxy-1-methylethyl)-2-propyl-, ethyl ester;OMSTint-D;)-2-propyL;Olmesartan Impurity 2
CBNumber:
CB4151009
Molecular Formula:
C12H20N2O3
Molecular Weight:
240.3
MOL File:
144689-93-0.mol
MSDS File:
SDS
Modify Date:
2024/6/15 22:11:33

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Properties

Melting point 98-100°C
Boiling point 456.2±35.0 °C(Predicted)
Density 1.131±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,2-8°C
solubility Chloroform, Ethyl Acetate, Methanol
form Solid
pka 11.61±0.10(Predicted)
color Pale Yellow
InChI InChI=1S/C12H20N2O3/c1-5-7-8-13-9(11(15)17-6-2)10(14-8)12(3,4)16/h16H,5-7H2,1-4H3,(H,13,14)
InChIKey KZBJJAFGNMRRHN-UHFFFAOYSA-N
SMILES C1(CCC)NC(C(OCC)=O)=C(C(O)(C)C)N=1
CAS DataBase Reference 144689-93-0(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
HS Code  2933.29.9000

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Chemical Properties,Uses,Production

Chemical Properties

Pale Yellow Solid

Application

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate is a synthetic drug with pharmacological properties that are similar to those of the natural product medoxomil. It has been shown to be a potent blocker of the GABA receptor and is used for the treatment of epilepsy.It has been shown to be an inhibitor of rat liver microsomes and also has a high affinity for the enzyme cilexetil, which is responsible for the conversion of cilexetil into its active form.

Synthesis

To a solution of MeMgCl(55.86 g, 0.74 mol) in tetrahydrofuran was added a solution of diethyl 2-propyl imidazole- 4,5-dicarboxylate (50 g,0.19 mol) in tetrahydrofuran (200 ml) at -10 to 0°C under N2 atmosphere. The mixture was stirred at -5 to 0°C for 10 minutes. The reaction mass was quenched into 400 ml 25 % ammonium chloride solution, followed by extraction with ethyl acetate (300 ml). The organic phase was separated, washed with brine, dried over Na2SO4, and concentrated in vacuo to give Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate, which was crystallized using diisopropyl ether. Yield: 85-90 %.
Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate

Definition

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate is a crucial intermediate for the synthesis of olmesartan medoxomil, which can be produced via the reaction of diethyl 2-propyl-imidazole-4,5-dicarboxylate, the raw material, with methylmagnesium bromide, followed by the acidification with saturated ammonium chloride solution.

Hazard

Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate is sensitive to the skin and may cause allergic skin reactions. It is irritating to the skin and eyes and may also cause respiratory irritation. It is poisonous to aquatic organisms.

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1H-Imidazole-4-carboxylicacid,5-(1-hydroxy-1-met 1H-Imidazole-5-carboxylicacid,4-(1-hydroxy-1-met 1H-Imidazole-4-carboxylic acid,5-(1-hydroxy-1-methylethyl)-2- propyl-,ethyl ester 4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-1H-IMIDAZOLE-5-CARBOXYLIC ACID ETHYL ESTER 98+% 5-(1-hydroxy-1-methylethyl)-2-propyl-,ethyl ester 4-(1-Hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid ethyl ester 4-(1-Hydroxy-1-methylethyl)-2-propyl- 5-(1-hydroxy-1-Methylethyl)-2-propyl-1H-IMidazole- 4-carboxylic acid ethyl ester 1H-Imidazole-4-carboxylic acid, 5-(1-hydroxy-1-methylethyl)-2-propyl-, ethyl ester (9CI) 5-(1-Hydroxy-1-Methyl-ethyl)-2-propyl-3H-iMidazole-4-carboxylic acid ethyl ester Ethyl 4-(2-Hydroxy-2-propyl)-2-propyl-1H-iMidazole-5-carboxylate OlMesartan IMidazole Ethyl Ester IMpurity 1h-iMdazole-4-carboxylic acid, 5-(1-hydroxy-1-Methylethyl)-2-propyl-,ethyl ester 1H-IMIDAZOLE-4-CARBOXYLIC ACID-5-(1-HYDROXY-1-METHYETHYL)-2-PROPYL-ETHYL ESTER OlMesartan IMpurity (Ethyl 4-(1-Hydroxy-1-Methylethyl)-2- Propyl-IMidazole-5-Carboxylate) 4-(2-Hydroxypropan-2-yl)-2-propyl-1H-iMidazole-5-carboxylic acid ethyl ester (EPIC) Ethyl 4-(1-hydroxy-1-Methylethyl)-2-propyliM... Ethyl 4-(2-Hydroxy-2-propyl)-2-propyl-1H-imidazole-5-carboxylate 4-(1-Hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid ethyl ester (OM-7) 4-(1-Hydroxy-isopropyl)-2-propyl-1H-imidazol-5-carboxylic acid ethyl ester Olmesartan Medoxomil Impurity 33 Olmesartan Medoxomil-18 OMSTint-D ethyl 5-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-4-carboxylate Olmesartan Impurity 2 Olmesartan Impurity 50 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate Ethyl4-(2-Hydroxy-2-propyl)-2-propyl-1H-imidazole-5-carboxylate> 4-(1-hydroxy-1-methyL 4-(1-Hydroxy-1-methylethyl)-2-Propyl-1H-Imiidazole 5-Carboxylic acid ethyl ester )-2-propyL 4-(2-hydroxy-2-propyl) -2-propyl-1H-imidazole-5-formate, ethyl ester 4-(2-Hydroxy-2-propyl)-2-propyl-1H-imidazole-5-carboxylic Acid Ethyl Ester Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate USP/EP/BP 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid ethyl ester for olmesartan 4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-1H-IMIDAZOLE-5-CARBOXYL IC ACID ETHYL ESTEROLE Imidazole-5-carboxylic ethyl ester [5-(1-Hydroxyl-1-methylethyl)-2-propyl-imidazol-4-yl]carboxy... Azilsartan medoxomil impurity230 4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-1H-IMIDAZOLE-5-CARBOXYLIC ACID ETHYL ESTER ETHYL-4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-IMIDAZOLE-5-CARBOXYLATE Olmesartan intermediate 5-(1-HYDROXYL-1-METHYLETHYL)-2-PROPYL-IMIDAZOL-4-YLCARBOXYLIC ACID ETHYL ESTER 1H-Imidazole-5-carboxylic acid, 4-(1-hydroxy-1-methylethyl)-2-propyl-, ethyl ester ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-iMidazole-5-carboxylate 4-(1-Hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate (Olmesartan Impurity) 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxyhio acid ethyl ester (1-Hydroxyl-1-methylethyl)-2-propyl-imidazol-4- yl]carboxylic acid ethyl ester Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carbo Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazol-5-carboxylate Ethyl 5-(1-Hydroxy-1-methyl-ethyl)-2-propyl-3H-imidazole-4-carboxylate Olmesartan ester impurity 27 Ethy-4-(1-Hydroxy-1-Mmethylethyl)-2-propylImidazole-5-Carboxylate. Ethyl5-(1-Hydroxy-1-methyl-ethyl)-2-propyl-3H-imidazole-4- carboxylate (Imidazole Ester) Olmesartan Imidazole Ethyl Ester Impurity Ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5- carboxylate OLM intermediate (4-(1-Hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid ethyl ester) 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-Imidazole