2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole

Base Information

• Chemical Name: 2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole
• CAS No.: 1431753-88-6
• Molecular Formula: C₂₁H₂₃NOS₆
• Molecular Weight: 497.816
• Mol file: 1431753-88-6.mol

Synonyms:2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole

Chemical Property of 2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole

There total 7 articles about 2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole 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: 72.0%

1-bromo-4-methoxy-benzene (104-92-7) + 2-(4,5-bis(propylthio)-(1,3)-dithiole-2-ylidene)-(1,3)-dithiolo[4,5-c]pyrrole → 2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole (1431753-88-6)

Guidance literature:

With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane; In 1,4-dioxane; at 110 ℃; Inert atmosphere;

DOI:10.1021/jo400502t

Reference yield:

carbonodithioic acid O-(isopropyl) S-(1-methyl-2-oxopropyl) ester (958649-73-5) → 2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole (1431753-88-6)

Guidance literature:

Multi-step reaction with 7 steps

1: sulfuric acid / Inert atmosphere

2: N-Bromosuccinimide / tetrachloromethane / Irradiation; Inert atmosphere

3: N,N-dimethyl-formamide / Inert atmosphere

4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / Inert atmosphere; Reflux

5: triethyl phosphite / 130 °C / Inert atmosphere

6: sodium methylate / tetrahydrofuran; methanol / Inert atmosphere

7: trans-1,2-Diaminocyclohexane; copper(l) iodide; potassium phosphate / 1,4-dioxane / 24 h / 110 °C / Inert atmosphere; Schlenk technique

With potassium phosphate; N-Bromosuccinimide; copper(l) iodide; sulfuric acid; trans-1,2-Diaminocyclohexane; sodium methylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; triethyl phosphite; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide; chlorobenzene; 7: |Ullmann Condensation;

DOI:10.3762/bjoc.11.96

Reference yield:

2-oxo-4,5-bis(bromomethyl)-1,3-dithiole (153911-38-7) → 2-[4,5-bis(propylthio)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole (1431753-88-6)

Guidance literature:

Multi-step reaction with 5 steps

1: N,N-dimethyl-formamide / Inert atmosphere

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / Inert atmosphere; Reflux

3: triethyl phosphite / 130 °C / Inert atmosphere

4: sodium methylate / tetrahydrofuran; methanol / Inert atmosphere

5: trans-1,2-Diaminocyclohexane; copper(l) iodide; potassium phosphate / 1,4-dioxane / 24 h / 110 °C / Inert atmosphere; Schlenk technique

With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane; sodium methylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; triethyl phosphite; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; chlorobenzene; 5: |Ullmann Condensation;

DOI:10.3762/bjoc.11.96

upstream raw materials:

1-bromo-4-methoxy-benzene

carbonodithioic acid O-(isopropyl) S-(1-methyl-2-oxopropyl) ester

4,5-dimethyl-[1,3]dithiol-2-one

2-oxo-4,5-bis(bromomethyl)-1,3-dithiole