41730-71-6

Basic information

• Product Name: 3-Acetyl-1-chlorocarbonyl-2-imidazolidone
• Synonyms: 3-ACETYL-2-OXO-1-IMIDAZOLIDINECARBONYL CHLORIDE;3-ACETYL-2-OXO-IMIDAZOLIDINE-1-CARBONYL CHLORIDE;3-acetyl-1-chlorocarbonyl-2-imidazolidone;3-ACETYL-1-CHLOROFORMYL-2-IMIDAZOLIDINONE;1-CHLOROCARBONYL-3-ACETYL-2-IMIDAZOLIDINONE;1-Chlorocarbonyl-3-acetyl-2-imidazolidone;3-Chlorocarbonyl-1-acetyl-2-imidazolidinone;3-ACETYL-2-IMIDAZOLIDINONE-1-CARBONYL CHLORIDE
• CAS NO: 41730-71-6
• Molecular Formula: C₆H₇ClN₂O₃
• Molecular Weight: 190.58
• Mol File: 41730-71-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 102-104°C
• Boiling Point: 278°C
• Flash Point: 122°C
• Appearance: /
• Density: 1.528
• Vapor Pressure: 0.00425mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: 3-Acetyl-1-chlorocarbonyl-2-imidazolidone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetyl-1-chlorocarbonyl-2-imidazolidone(41730-71-6)
• EPA Substance Registry System: 3-Acetyl-1-chlorocarbonyl-2-imidazolidone(41730-71-6)

Safety Data

• Hazardous Substances Data: 41730-71-6(Hazardous Substances Data)

Usage

General Description

3-Acetyl-1-chlorocarbonyl-2-imidazolidone is a chemical compound that is used as a reagent in organic synthesis and pharmaceutical research. It is a white to pale yellow solid with a molecular formula C6H8ClNO3 and a molecular weight of 171.6 g/mol. 3-Acetyl-1-chlorocarbonyl-2-imidazolidone is known for its versatile reactivity, particularly in the formation of imidazolidene intermediates, which can be used in the synthesis of various pharmaceutical and agrochemical products. Additionally, it has been studied for its potential antimicrobial and antifungal properties, making it a potentially valuable compound in the development of new drugs and medical treatments. Overall, 3-Acetyl-1-chlorocarbonyl-2-imidazolidone is a versatile and promising chemical with a wide range of potential applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C6H7ClN2O3/c1-4(10)8-2-3-9(5(7)11)6(8)12/h2-3H2,1H3

Synthetic route

1-acetylimidazolidin-2-one (5391-39-9) + bis(trichloromethyl) carbonate (32315-10-9) → 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine (41730-71-6)

Conditions	Yield
In benzene at 55 - 60℃; for 3h; chloroformylation;	93.8%

1-acetylimidazolidin-2-one (5391-39-9) + trichloromethyl chloroformate (503-38-8) → 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine (41730-71-6)

Conditions	Yield
With pyridine In benzene at 50 - 55℃; for 2h; Addition;	92%

7-(D-α-aminophenylacetamido)-3-(5-methyl-1,3,4-thiadiazole-2-yl)thiomethyl-3-cephem-4-carboxylic acid → Sodium 7-[D-α-(3-acetylimidazolidin-2-on-1-ylcarbonylamino)phenylacetamido]-3-(2-methyl-1,3,4-thiadiazol-5-ylthio)methylceph-3-em-4-carboxylate + 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine (41730-71-6)

Conditions	Yield
	A n/a B 74.3%

7-(D(-)-α-amino-α-phenylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid → Sodium 7-[D-α-(3-acetylimidazolidin-2-on-1-ylcarbonylamino)phenylacetamido]-3-(1-methyl-1H-tetrazol-5-ylthio)methylceph-3-em-4-carboxylate + 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine (41730-71-6)

Conditions	Yield
	A n/a B 43.5%

ampicillin (69-53-4) + 1-chlorocarbonyl-2-oxo-3-methylcarbonyl-imidazolidine (41730-71-6) + sodium 2-ethylhexanoic acid → penicillin G (61-33-6)

Conditions	Yield
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate	95%
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate	95%
With triethylamine In methanol; aqueous tetrahydrofurane; water; ethyl acetate	95%

Upstream product

• 5391-39-9 1-acetylimidazolidin-2-one 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 61-33-6 penicillin G 

Relevant articles and documents

The preparation of 3-substituted 1-chlorocarbonyl-imidazolidin-2-ones using bis(trichloromethyl) carbonate

A novel synthesis of 3-substituted 1-chlorocarbonyl-imidazolidin-2-ones using bis(trichloromethyl) carbonate is reported. The bis(trichloromethyl)carbonate is used to generate phosgene in situ in stoichiometric amounts. The yields and purity of the products obtained are better than those obtained by a conventional way using phosgene.

α-Acylureidocephalosporins and salts and esters thereof

Compounds which are clinically important cephalosporins and salts and esters thereof having a wide spectrum of activity against Gram-positive bacteria but especially against Gram-negative bacteria such as Pseudomonas spp. against which commercially available cephalosporins are normally inactive. Preferred compounds of the invention are also active against Gram-negative cephalosporinase-producing organisms such as Enterobacter spp., Serratia spp. and indole-positive Proteus; methods of preparation are described.

Cephalosporins and their production

Cephalosporins of the formula STR1 their pharmaceutically-acceptable, nontoxic salts, and hydrates thereof are produced, wherein A is hydrogen; unsubstituted or substituted alkyl; aryl; or R1 --X--, wherein X is --CO-- or --SO2 --, and R1 is hydrogen, unsubstituted or substituted alkyl; aryl; thienyl; furyl; amino; alkylamino; dialkylamino; pyrrolidyl; or piperidyl; Or when X is --CO--, R1 can also be alkoxy; B is phenyl, methylphenyl, chlorophenyl, hydroxyphenyl or the moiety STR2 E is hydrogen, hydroxyl or acetoxy; and C is a center of chirality. These compounds are particularly useful for their antimicrobial and, particularly, antibacterial effects.