1-((2'-Carboxybiphenyl-4-yl)methyl)-2-(1-butenyl)-4-chloro-5-hydroxymethylimidazole

Base Information

• Chemical Name: 1-((2'-Carboxybiphenyl-4-yl)methyl)-2-(1-butenyl)-4-chloro-5-hydroxymethylimidazole
• CAS No.: 114798-32-2
• Molecular Formula: C22H21 Cl N2 O3
• Molecular Weight: 396.873
• DSSTox Substance ID: DTXSID60921500
• Mol file: 114798-32-2.mol

Synonyms:Exp9270;Exp 9270;DTXSID60921500;1-((2'-Carboxybiphenyl-4-yl)methyl)-2-(1-butenyl)-4-chloro-5-hydroxymethylimidazole;4'-{[2-(But-1-en-1-yl)-4-chloro-5-(hydroxymethyl)-1H-imidazol-1-yl]methyl}[1,1'-biphenyl]-2-carboxylic acid

Chemical Property of 1-((2'-Carboxybiphenyl-4-yl)methyl)-2-(1-butenyl)-4-chloro-5-hydroxymethylimidazole

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 396.1240702
• Heavy Atom Count: 28
• Complexity: 536

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C(=O)O)CO)Cl

Technology Process of 1-((2'-Carboxybiphenyl-4-yl)methyl)-2-(1-butenyl)-4-chloro-5-hydroxymethylimidazole

There total 16 articles about 1-((2'-Carboxybiphenyl-4-yl)methyl)-2-(1-butenyl)-4-chloro-5-hydroxymethylimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-(1-trans-butenyl)-4-chloro-5-hydroxymethylimidazole (114772-69-9) → 2-(1E-Butenyl)-4-chloro-1-[(2'-carboxybiphenyl-4-yl)methyl]-5-(hydroxymethyl)imidazole (114798-32-2)

Guidance literature:

With sodium hydroxide; In ethanol; for 14h; Heating;

DOI:10.1021/jm00112a031

Reference yield:

2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (57598-33-1) → 2-(1E-Butenyl)-4-chloro-1-[(2'-carboxybiphenyl-4-yl)methyl]-5-(hydroxymethyl)imidazole (114798-32-2)

Guidance literature:

Multi-step reaction with 10 steps

1: tetrahydrofuran / 2 h / 20 °C

2: 88 percent / 4.5 N aq. HCl / 12 h / Heating

3: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h

4: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating

5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h

6: 56 percent / manganese dioxide / CH₂Cl₂ / 40 h / 25 °C

7: 40 percent / N-bromosuccinimide / CCl₄ / 0.5 h / Irradiation

8: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C

9: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C

10: 10percent aq. NaOH / ethanol / 14 h / Heating

With hydrogenchloride; manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane;

DOI:10.1021/jm00112a031

Reference yield:

4-tolyl iodide (624-31-7) → 2-(1E-Butenyl)-4-chloro-1-[(2'-carboxybiphenyl-4-yl)methyl]-5-(hydroxymethyl)imidazole (114798-32-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 11 percent / Cu / 1 h / 210 °C

2: N-bromosuccinimide, dibenzoyl peroxide / CCl₄ / 3 h / Heating

3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h

4: 56 percent / manganese dioxide / CH₂Cl₂ / 40 h / 25 °C

5: 40 percent / N-bromosuccinimide / CCl₄ / 0.5 h / Irradiation

6: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C

7: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C

8: 10percent aq. NaOH / ethanol / 14 h / Heating

With manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; copper; 1,8-diazabicyclo[5.4.0]undec-7-ene; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane;

DOI:10.1021/jm00112a031

upstream raw materials:

1-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-(1-trans-butenyl)-4-chloro-5-hydroxymethylimidazole

2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline

4-tolyl iodide

o-iodo-methyl-benzoic acid