(E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide

Base Information

Chemical Name:(E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide
CAS No.:119680-41-0
Molecular Formula:C₁₆H₂₁NO₃S
Molecular Weight:307.414
Hs Code.:

Synonyms:(E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide

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Chemical Property of (E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide

Chemical Property:

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Technology Process of (E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide

There total 7 articles about (E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide 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: 50.0%

: 119680-40-9
(E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenamide

: 119680-41-0
(E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide

Guidance literature:: With Lawessons reagent; In tetrahydrofuran; for 18h;
DOI:10.1021/jo00269a024

Reference yield:

: 35493-66-4
methyl 3-(methoxycarbonyl)-2-methyl-4-oxopentanoate

: 119680-41-0
(E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / H₂ / PtO₂ / ethyl acetate / 2327.2 Torr

2: KH, MeOH / diethyl ether / 4 h / Heating

3: oxalyl chloride, DMF / acetonitrile / 1.) 0 deg C, 15 min, 2.) -22 deg C, 15 min

4: acetonitrile; dimethylformamide / 1.) -22 deg C, 5 min, 2.) room temp., 1 h

5: 50 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / tetrahydrofuran / 18 h

With Lawessons reagent; methanol; oxalyl dichloride; hydrogen; potassium hydride; N,N-dimethyl-formamide; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00269a024

Reference yield:

: 105-45-3
acetoacetic acid methyl ester

: 119680-41-0
(E)-N-(p-methoxybenzyl)-3-(methoxycarbonyl)-2-methyl-3-pentenethioamide

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaOMe / 1.) MeOH, 30 min, 2.) MeOH, reflux, 3 h

2: 86 percent / H₂ / PtO₂ / ethyl acetate / 2327.2 Torr

3: KH, MeOH / diethyl ether / 4 h / Heating

4: oxalyl chloride, DMF / acetonitrile / 1.) 0 deg C, 15 min, 2.) -22 deg C, 15 min

5: acetonitrile; dimethylformamide / 1.) -22 deg C, 5 min, 2.) room temp., 1 h

6: 50 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) / tetrahydrofuran / 18 h

With Lawessons reagent; methanol; oxalyl dichloride; hydrogen; sodium methylate; potassium hydride; N,N-dimethyl-formamide; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00269a024