(+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]benzoate

Base Information

• Chemical Name: (+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]benzoate
• CAS No.: 259794-38-2
• Molecular Formula: C₂₁H₁₈N₂O₅S
• Molecular Weight: 410.45

Synonyms:(+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]benzoate

Chemical Property of (+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]benzoate

Chemical Property:

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Technology Process of (+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]benzoate

There total 4 articles about (+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ⁶,2,5-thiadiazolan-2-yl]benzoate 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: 51.0%

(+/-)-methyl 4-[({[1-(methoxycarbonyl)-2-(naphthalen-2-yl)ethyl]amino}sulfonyl)amino]benzene-1-carboxylate (259794-34-8) → (+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ6,2,5-thiadiazolan-2-yl]benzoate (259794-38-2)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; pentane; at 20 ℃; for 12h;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

Reference yield:

4-sulfoamino-benzoic acid methyl ester (772337-11-8) → (+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ6,2,5-thiadiazolan-2-yl]benzoate (259794-38-2)

Guidance literature:

Multi-step reaction with 3 steps

1: PCl₅ / CH₂Cl₂ / 3.5 h / Heating

2: 95 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C / pH 8 - 9

3: 51 percent / t-BuLi / pentane; tetrahydrofuran / 12 h / 20 °C

With phosphorus pentachloride; tert.-butyl lithium; triethylamine; In tetrahydrofuran; dichloromethane; pentane; 1: Substitution / 2: Condensation / 3: Cyclization;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

Reference yield:

4-methoxycarbonyl aniline (619-45-4) → (+/-)-methyl 4-[4-(naphthalen-2-ylmethyl)-1,1,3-trioxo-1λ6,2,5-thiadiazolan-2-yl]benzoate (259794-38-2)

Guidance literature:

Multi-step reaction with 4 steps

1: ClSO₃H / CH₂Cl₂ / 1 h / 20 °C

2: PCl₅ / CH₂Cl₂ / 3.5 h / Heating

3: 95 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C / pH 8 - 9

4: 51 percent / t-BuLi / pentane; tetrahydrofuran / 12 h / 20 °C

With chlorosulfonic acid; phosphorus pentachloride; tert.-butyl lithium; triethylamine; In tetrahydrofuran; dichloromethane; pentane; 1: Condensation / 2: Substitution / 3: Condensation / 4: Cyclization;

DOI:10.1002/(SICI)1522-2675(19991215)82:12<2432::AID-HLCA2432>3.0.CO;2-H

upstream raw materials:

(+/-)-methyl 4-[({[1-(methoxycarbonyl)-2-(naphthalen-2-yl)ethyl]amino}sulfonyl)amino]benzene-1-carboxylate

4-sulfoamino-benzoic acid methyl ester

4-methoxycarbonyl aniline

methyl 4-chlorosulfonylaminobenzoate

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