147-52-4

Basic information

• Product Name: nafcillin
• Synonyms: (2S,5R,6R)-6-(2-Ethoxy-1-naphthoylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6α-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]penicillanic acid;C07250;Nafcillin acid;6-(2-Ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Nafcilin 1;Westwood acid, naphthalene
• CAS NO: 147-52-4
• Molecular Formula: C21H22N2O5S
• Molecular Weight: 414.48
• EINECS: 205-690-9
• Mol File: 147-52-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 714.1 °C at 760 mmHg
• Flash Point: 385.7 °C
• Appearance: /
• Density: 1.42 g/cm³
• Vapor Pressure: 4.28E-21mmHg at 25°C
• PKA: 2.44±0.50(Predicted)
• CAS DataBase Reference: nafcillin(CAS DataBase Reference)
• NIST Chemistry Reference: nafcillin(147-52-4)
• EPA Substance Registry System: nafcillin(147-52-4)

Safety Data

• Hazardous Substances Data: 147-52-4(Hazardous Substances Data)

Usage

Originator

Unipen,Wyeth,US,1964

Uses

Antibacterial.

Manufacturing Process

A stirred suspension of 12.6 grams 6-aminopenicillanic acid in 130 ml dry alcohol-free chloroform was treated with 16 ml triethylamine and then with 13.8 grams of a solution of 2-ethoxy-1-naphthoyl chloride in 95 ml chloroform. After being washed successively with 58 ml each of 1 N and then 0.1 N hydrochloric acid the chloroform solution was extracted with N aqueous sodium bicarbonate (58 ml + 6 ml). The combined bicarbonate extracts were washed with 20 ml ether and then evaporated at low temperature and pressure to give the crude sodium salt of 2-ethoxy-1-naphthylpenicillin [also called sodium 6-(2-ethoxy-1-naphthamido)penicillinate] as a yellow powder (20.3 grams). This was dissolved in 20 ml water at 30°C and diluted with 180 ml n-butanol, also at 30°C, with stirring. Slow cooling to 0°C gave colorless needles of the product.

Brand name

Nallpen (GlaxoSmithKline).

Therapeutic Function

Antibacterial

InChI:InChI=1/C21H22N2O5S.Na/c1-4-28-13-10-9-11-7-5-6-8-12(11)15(13)22-17(24)14-18(25)23-16(20(26)27)21(2,3)29-19(14)23;/h5-10,14,16,19H,4H2,1-3H3,(H,22,24)(H,26,27);/q;+1/p-1/t14-,16?,19-;/m1./s1

Upstream product

• 2224-00-2 2-ethoxy-1-naphthaloic acid 
• 53446-67-6 2-ethoxy-naphthalene-1-carboxylic acid; sodium salt 
• 53388-50-4 6β-[(2-ethoxy-naphthalene-1-carbonyl)-phenylacetyl-amino]-penicillanic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester 
• 551-16-6 6-Aminopenicillanic Acid 
• 55150-29-3 2-ethoxynaphthalenyl-1-carbonyl chloride 
• 27605-28-3 6β-(2-phenyl-acetylamino)-penicillanic acid 2-(4-bromo-phenyl)-2-oxo-ethyl ester 

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Relevant articles and documents

A preparation method of naphthalene husband xilin acid

The invention discloses a method for preparing nafcillin acid. The method comprises the following steps: (1) chlorinating 2-ethoxy naphthoic acid and excessive amount of sulfoxide chloride to obtain an acyl chloride solution; carrying out distillation at reduced pressure to remove sulfoxide chloride, dissolving residues with dichloromethane, and thus obtaining a mixed solution A; (2) adding triethylamine and dichloromethane in 6-aminopenicillanic acid, stirring until the solution is clear, and thus obtaining a mixed solution B; (3) dropwise adding the mixed solution A in the mixed solution B for condensation reaction, carrying out thermal reaction for 30-90 min after the mixed solution A completely is dropwise added in the mixed solution B, and thus obtaining a mixed solution C; (4) concentrating the mixed solution C to be dry, and thus obtaining a solid mixture D; (5) stirring and dispersing the solid mixture D with a ketone reagent, acidizing with an acidifier, adding an ether reagent to stir, filtering, adding purified water or saturated salt water in filtrate to crystallize, filtering, washing with water, drying, and thus obtaining nafcillin acid. The method has the advantages of being simple in process, easy to operate, simple in postprocessing and high in yield.

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