4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester

Base Information

Chemical Name:4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester
CAS No.:148674-53-7
Molecular Formula:C₂₄H₂₅N₃O₂S
Molecular Weight:419.547
Hs Code.:

Synonyms:4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester

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Chemical Property of 4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester

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Technology Process of 4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester

There total 13 articles about 4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester 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: 78.0%

: 148674-45-7
(E)-3-<2-butyl-1-<(4-carbomethoxyphenyl)methyl>imidazol-5-yl>-2-(2-thienylmethyl)-2-propenamide

: 148674-53-7
4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester

Guidance literature:: With oxalyl dichloride; N,N-dimethyl-formamide; In acetonitrile; for 0.0833333h;
DOI:10.1021/jm00065a011

Reference yield:

: 98-03-3
thiophene-2-carbaldehyde

: 148674-53-7
4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: sodium hydride / 1.) DME, RT, 30 min, 2.) DME, 2.5 h

2: hydrogen / palladium on activated charcoal / ethyl acetate / 18 h / 2585.7 Torr

3: lithium diisopropyl amide / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 5 min

4: dmap / 16 h

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0.67 h / 110 °C

6: trifluoroacetic acid / dichloromethane / 5 h / Ambient temperature

7: thionyl chloride / benzene / 2.5 h / 55 °C

8: ammonium hydroxide / 1 h / Ambient temperature

9: oxalyl dichloride; N,N-dimethyl-formamide / acetonitrile / 0.08 h

With dmap; ammonium hydroxide; thionyl chloride; oxalyl dichloride; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In dichloromethane; ethyl acetate; toluene; acetonitrile; benzene;
DOI:10.1021/jm00065a011

Reference yield:

: 2417-72-3
Methyl 4-(bromomethyl)benzoate

: 148674-53-7
4-[2-Butyl-5-((E)-2-cyano-3-thiophen-2-yl-propenyl)-imidazol-1-ylmethyl]-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 70 °C

2: manganese(IV) oxide; hydrogen; potassium acetate / palladium on activated charcoal / 1.) MeOH, 40 psi, 1.25 h, 2.) CH₂Cl₂, reflux

3: lithium diisopropyl amide / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 5 min

4: dmap / 16 h

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0.67 h / 110 °C

6: trifluoroacetic acid / dichloromethane / 5 h / Ambient temperature

7: thionyl chloride / benzene / 2.5 h / 55 °C

8: ammonium hydroxide / 1 h / Ambient temperature

9: oxalyl dichloride; N,N-dimethyl-formamide / acetonitrile / 0.08 h

With dmap; manganese(IV) oxide; ammonium hydroxide; thionyl chloride; oxalyl dichloride; hydrogen; potassium acetate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1021/jm00065a011