N-(2-Cyano-2-(triphenylphosphoranylidene)ethanethioyl)benzamide

Base Information

• Chemical Name: N-(2-Cyano-2-(triphenylphosphoranylidene)ethanethioyl)benzamide
• CAS No.: 155786-93-9
• Molecular Formula: C28H21N2OPS
• Molecular Weight: 464.527
• DSSTox Substance ID: DTXSID30395113
• Wikidata: Q82194952
• Mol file: 155786-93-9.mol

Synonyms:155786-93-9;N-(2-Cyano-2-(triphenylphosphoranylidene)ethanethioyl)benzamide;DTXSID30395113;STK370933;AKOS001019057;AKOS002663114;UPCMLD0ENAT0506-3786:001;Z56812998;T0506-3786;(Z)-2-cyano-1-[(phenylcarbonyl)amino]-2-(triphenylphosphonio)ethenethiolate

Chemical Property of N-(2-Cyano-2-(triphenylphosphoranylidene)ethanethioyl)benzamide

Chemical Property:

• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 464.11122147
• Heavy Atom Count: 33
• Complexity: 736

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC(=S)C(=P(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C#N

Technology Process of N-(2-Cyano-2-(triphenylphosphoranylidene)ethanethioyl)benzamide

There total 1 articles about N-(2-Cyano-2-(triphenylphosphoranylidene)ethanethioyl)benzamide 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: 96.0%

Benzoyl isothiocyanate (532-55-8) + cyanomethylene triphenylphosphorane (16640-68-9) → 2-benzoylamino-1-cyano-2-thioxoethylidenetriphenylphosphorane (155786-93-9)

Guidance literature:

In acetonitrile; at 50 - 70 ℃; for 1h;

DOI:10.1023/B:RUGC.0000045875.40116.eb

Reference yield: 64.0%

2-benzoylamino-1-cyano-2-thioxoethylidenetriphenylphosphorane (155786-93-9) → (4-Mercapto-6-oxo-2-phenyl-1,6-dihydro-pyrimidin-5-yl)-triphenyl-phosphonium; chloride

Guidance literature:

With hydrogenchloride; In methanol; at 20 - 25 ℃; for 5h;

Reference yield:

2-benzoylamino-1-cyano-2-thioxoethylidenetriphenylphosphorane (155786-93-9) → 6-Methylsulfanyl-2-phenyl-5-(triphenyl-λ5-phosphanylidene)-5H-pyrimidin-4-one (180848-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂SO₄ / methanol / 45 - 50 °C

1.2: 90 percent / Et₃N / methanol; ethanol / 50 - 60 °C

2.1: 94 percent / acetonitrile / 20 - 25 °C

3.1: 78 percent / NaOH / ethanol / 50 - 60 °C

With sodium hydroxide; sulfuric acid; In methanol; ethanol; acetonitrile;

DOI:10.1023/B:RUGC.0000045875.40116.eb

upstream raw materials:

Benzoyl isothiocyanate

cyanomethylene triphenylphosphorane

Downstream raw materials:

6-benzylsulfanyl-2-phenyl-5-(triphenyl-λ⁵-phosphanylidene)-5H-pyrimidin-4-one