5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione

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Chemical Name:5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione
CAS No.:943141-67-1
Molecular Formula:C₃₃H₃₀ClNO₃S
Molecular Weight:556.125
Hs Code.:

Synonyms:5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione

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Chemical Property of 5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione

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Technology Process of 5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione

There total 8 articles about 5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione 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: 62.0%

: 943141-66-0
4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzaldehyde

: 2295-31-0
thiazoline-2,4-dione

: 943141-67-1
5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione

Guidance literature:: With acetic acid; diethylamine; In toluene; for 2h; Heating;
DOI:10.1021/jm0613323

Reference yield:

: 736992-49-7
2-(1-adamantyl)-1-benzyloxy-4-bromobenzene

: 943141-67-1
5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C

1.3: 89 percent / aq. HCl / tetrahydrofuran; hexane

2.1: 78 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

3.1: 62 percent / HOAc; NHEt₂ / toluene / 2 h / Heating

With n-butyllithium; sodium carbonate; acetic acid; diethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; toluene; 2.1: Suzuki-Miyaura coupling;
DOI:10.1021/jm0613323

Reference yield:

: 106-41-2
4-bromo-phenol

: 943141-67-1
5-{4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorobenzylidene}-1H-2,4-thiazolidinedione

Guidance literature:: Multi-step reaction with 5 steps

1.1: conc. sulfuric acid / CH₂Cl₂

2.1: K₂CO₃ / acetone / Heating

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C

3.3: 89 percent / aq. HCl / tetrahydrofuran; hexane

4.1: 78 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

5.1: 62 percent / HOAc; NHEt₂ / toluene / 2 h / Heating

With n-butyllithium; sodium carbonate; potassium carbonate; acetic acid; diethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; toluene; 1.1: Friedel-Crafts alkylation / 4.1: Suzuki-Miyaura coupling;
DOI:10.1021/jm0613323