(R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one

Base Information

• Chemical Name: (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one
• CAS No.: 321724-08-7
• Molecular Formula: C₂₀H₁₃Cl₂IN₄O
• Molecular Weight: 523.16
• Mol file: 321724-08-7.mol

Synonyms:(R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one

Chemical Property of (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one

There total 10 articles about (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one 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:

(R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a]-imidazol-2-one (321657-06-1) → (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one (321724-08-7)

Guidance literature:

With N-iodo-succinimide; pyridinium p-toluenesulfonate; In dichloromethane; at -20 - 20 ℃;

Reference yield:

phosphoric acid 5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazol-3-yl ester diethyl ester (835917-17-4) → (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one (321724-08-7)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In dichloromethane; water; at 20 - 25 ℃; for 0.333333h;

DOI:10.1016/j.tetlet.2004.11.065

Reference yield:

4-cyanobenzyl bromide (17201-43-3) → (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-imidazo[1,2-a]-imidazol-2-one (321724-08-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LHMDS / tetrahydrofuran / -15 °C

2.1: BnMe₃NOH; NaOH / dioxane / 45 °C

2.2: aq. HCl / 50 °C

3.1: tBuCOCl / tetrahydrofuran / 0 - 10 °C

4.1: TsOH*H₂O / methanol / 50 °C

5.1: tetrahydrofuran / 20 - 35 °C

6.1: CuCl; iPr₂NEt; Celite / toluene; acetonitrile / 0.5 h / 80 °C

7.1: LHMDS / tetrahydrofuran / -10 °C

8.1: TMSCl; NaI / H₂O; CH₂Cl₂ / 0.33 h / 20 - 25 °C

With sodium hydroxide; chloro-trimethyl-silane; Celite; pivaloyl chloride; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; sodium iodide; copper(l) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/j.tetlet.2004.11.065

upstream raw materials:

phosphoric acid 5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazol-3-yl ester diethyl ester

4-cyanobenzyl bromide

(2R,5R)-3-(3,5-dichlorophenyl)-2-isopropyl-5-methyl-1-(2,2,2-trichloroacetyl)-imidazolidin-4-one

2-amino-3-(4-cyano-phenyl)-N-(3,5-dichloro-phenyl)-2-methyl-propionamide

Downstream raw materials:

(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl chloride