2-(3,4-Dichlorophenyl)-N-methyl-N-(1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl)acetamide

Base Information

• Chemical Name: 2-(3,4-Dichlorophenyl)-N-methyl-N-(1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl)acetamide
• CAS No.: 155512-49-5
• Molecular Formula: C₂₂H₂₃Cl₂N₃OS
• Molecular Weight: 448.416
• DSSTox Substance ID: DTXSID80935225
• Nikkaji Number: J628.187G
• ChEMBL ID: CHEMBL38521
• Mol file: 155512-49-5.mol

Synonyms:2-(3,4-dichlorophenyl)-N-methyl-N-(1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl)acetamide;DIPPA

Chemical Property of 2-(3,4-Dichlorophenyl)-N-methyl-N-(1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl)acetamide

Chemical Property:

• Vapor Pressure: 9.12E-15mmHg at 25°C
• Boiling Point: 608.8°Cat760mmHg
• Flash Point: 322°C
• PSA: 68.00000
• Density: 1.27g/cm³
• LogP: 5.50360
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 447.0938889
• Heavy Atom Count: 29
• Complexity: 595

Purity/Quality:

99%,98%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(CN1CCCC1)C2=CC(=CC=C2)N=C=S)C(=O)CC3=CC(=C(C=C3)Cl)Cl
• Isomeric SMILES: CN([C@H](CN1CCCC1)C2=CC(=CC=C2)N=C=S)C(=O)CC3=CC(=C(C=C3)Cl)Cl

Technology Process of 2-(3,4-Dichlorophenyl)-N-methyl-N-(1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl)acetamide

There total 5 articles about 2-(3,4-Dichlorophenyl)-N-methyl-N-(1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl)acetamide 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:

2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-(3-nitrophenyl)-2-(pyrrolidin-1-yl)ethyl]acetamide (155512-51-9) → 2-(3,4-dichlorophenyl)-N-methyl-N-<(1S)-1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl>acetamide (155512-49-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / hydrazine / Raney Ni / aq. ethanol / 2.5 h / 55 °C

2: aq. NaHCO₃ / tetrahydrofuran / 25 °C

With sodium hydrogencarbonate; hydrazine; nickel; In tetrahydrofuran; ethanol;

DOI:10.1021/jm00052a008

Reference yield:

2-(3,4-dichlorophenyl)acetyl chloride (6831-55-6) → 2-(3,4-dichlorophenyl)-N-methyl-N-<(1S)-1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl>acetamide (155512-49-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) conc. H₂SO₄, conc. HNO₃, 2.) Et₃N / 1.) 45 min, 2.) CH₂Cl₂, 25 deg C, 21 h

2: 100 percent / hydrazine / Raney Ni / aq. ethanol / 2.5 h / 55 °C

3: aq. NaHCO₃ / tetrahydrofuran / 25 °C

With sulfuric acid; nitric acid; sodium hydrogencarbonate; triethylamine; hydrazine; nickel; In tetrahydrofuran; ethanol;

DOI:10.1021/jm00052a008

Reference yield:

thiophosgene (463-71-8) + N-[(1S)-1-(3-aminophenyl)-2-(pyrrolidin-1-yl)ethyl]-2-(3,4-dichlorophenyl)-N-methylacetamide (155551-42-1) → 2-(3,4-dichlorophenyl)-N-methyl-N-<(1S)-1-(3-isothiocyanatophenyl)-2-(1-pyrrolidinyl)ethyl>acetamide (155512-49-5)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran;

DOI:10.1021/jm00037a001

upstream raw materials:

thiophosgene

N-[(1S)-1-(3-aminophenyl)-2-(pyrrolidin-1-yl)ethyl]-2-(3,4-dichlorophenyl)-N-methylacetamide

3,4-dichlorophenyl acetic acid

2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-(3-nitrophenyl)-2-(pyrrolidin-1-yl)ethyl]acetamide