2-chloro-N-(2-methylphenyl)propanamide

Base Information

• Chemical Name: 2-chloro-N-(2-methylphenyl)propanamide
• CAS No.: 19281-31-3
• Molecular Formula: C10H12ClNO
• Molecular Weight: 197.664
• Hs Code.: 2924299090
• UNII: 3K1086IX8P
• Nikkaji Number: J2.286.739C
• Wikidata: Q27257360
• Mol file: 19281-31-3.mol

Synonyms:2-chloro-N-(2-methylphenyl)propanamide;19281-31-3;2-Chloro-N-(o-tolyl)propanamide;2-Chloro-o-propionotoluidide;Propanamide, 2-chloro-N-(2-methylphenyl)-;o-Propionotoluidide, 2-chloro-;(RS)-2-Chloro-N-(2-methylphenyl)propanamide;Prilocaine impurity A [EP];UNII-3K1086IX8P;3K1086IX8P;MFCD06356479;Prilocaine hydrochloride impurity A [EP];SCHEMBL6243373;BBL037317;STK501998;AKOS000200673;AKOS016340929;N-(2-Methylphenyl)-2-chloropropionamide;SY131962;VS-14067;PRILOCAINE IMPURITY A [EP IMPURITY];BB 0218496;CS-0307854;EN300-09007;E78030;A880304;J-509059;Q27257360;Z56346852;PRILOCAINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]

Chemical Property of 2-chloro-N-(2-methylphenyl)propanamide

Chemical Property:

• PSA: 29.10000
• LogP: 2.63380
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 197.0607417
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-o-propionotoluidide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1NC(=O)C(C)Cl
• Uses: 2-Chloro-o-propionotoluidide (Prilocaine EP Impurity A) is an impurity of Prilocaine, a local anesthetic to treat paresthesia.

Technology Process of 2-chloro-N-(2-methylphenyl)propanamide

There total 6 articles about 2-chloro-N-(2-methylphenyl)propanamide 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: 95.0%

o-toluidine (95-53-4) + (R,S)-2-chloropropionic acid (598-78-7) → N-(2-methylphenyl)-2-chloropropanamide (19281-31-3)

Guidance literature:

(R,S)-2-chloropropionic acid; With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; In N,N-dimethyl-formamide; for 0.25h;

o-toluidine; With 4-methyl-morpholine; In water; N,N-dimethyl-formamide; at 0 - 10 ℃; for 6.25h;

Reference yield: 67.0%

2-chloropropionyl chloride (7623-09-8) + N-(2-methylphenyl)acetamide (120-66-1) → N-(2-methylphenyl)-2-chloropropanamide (19281-31-3)

Guidance literature:

With aluminium trichloride; In 1,2-dichloro-ethane; for 16h;

DOI:10.1039/a705770i

Reference yield:

o-toluidine (95-53-4) → N-(2-methylphenyl)-2-chloropropanamide (19281-31-3)

Guidance literature:

Multi-step reaction with 2 steps

2: benzene; PCl₅ / man destilliert darauf bei 140-160grad unter 40-60 mm Druck; das hierbei erhaltene Oel zersetzt man mit Wasser

With phosphorus pentachloride; benzene;

upstream raw materials:

DL-lactic acid o-toluidide

2-chloropropionyl chloride

N-(2-methylphenyl)acetamide

phosphorus pentachloride

Downstream raw materials:

prilocaine

2-methyl-4-o-tolyl-2H-1,4-benzoxazin-3(4H)-one

(5-methyl-4-oxo-3-o-tolyl-thiazolidin-2-ylidene)-cyanamide

Refernces

• 1、 Sonawane,Pol,Nanjundiah,Sudalai. "AlCl3-Catalysed trans N-acylation of Acetanilides with α-Chloropropionyl Chloride". . p. 90 - 91. Retrieved 2007/10/03.