41730-71-6

Usage

Uses

Used in Pharmaceutical Research and Organic Synthesis:
3-Acetyl-1-chlorocarbonyl-2-imidazolidone is used as a reagent for its versatile reactivity in the formation of imidazolidene intermediates, which are essential in the synthesis of a wide range of pharmaceutical and agrochemical products.
Used in Antimicrobial and Antifungal Drug Development:
3-Acetyl-1-chlorocarbonyl-2-imidazolidone is studied for its potential antimicrobial and antifungal properties, making it a promising compound for the development of new drugs and medical treatments to combat resistant infections.
Used in Chemical Industry:
3-Acetyl-1-chlorocarbonyl-2-imidazolidone is utilized in the chemical industry for its wide range of potential applications, including the synthesis of various compounds and the development of innovative products.

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 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 61-33-6 penicillin G 

Relevant academic research and scientific papers

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.

Oxo-imidazolidine substituted cephalosporins and antibacterial compositions and methods of combatting bacteria employing them

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.

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.

Penicillins

Penicillins of the formula EQU1 or pharmaceutically acceptable non-toxic salts thereof, wherein C is a carbon atom constituting a center of chirality; A is a moiety of the formula EQU2 or EQU3 wherein X is EQU4 Y is EQU5 or wherein Aryl is an aryl moiety; Z is EQU6 Q1 is EQU7 or SPC1 Q2 is EQU8 SPC2 or SPC3 R is straight-chain or branched alkyl of 1 to 5 carbon atoms; R1 is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkenyl of 3 to 10 carbon atoms, vinyl, arylvinyl, mono-, di-, or tri-halo-lower alkyl, H2 N--, R--NH--, (R)2 N--, aryl--NH--, aryl-lower alkylamino, alkoxy of 1 to 8 carbon atoms, aralkoxy of 1 to 8 carbon atoms in the alkoxy portion, cycloalkoxy of 3 to 7 carbon atoms, aryloxy, R--O--V--, R--S-- V--, N=C--V--, R--O--CO--V--, H2 N--CO--V--, R--NH--CO--V--, R--O--CO--NH--, R--SO2 --NH--, (R)2 N--CO--V--, wherein R is as above defined, SPC4 SPC5 provided that when X is --SO2 --, R1 is not alkoxy, aralkoxy, cycloalkoxy or aryloxy, and further provided that R1 can also be hydrogen when X is --CO--; V is a divalent organic radical of 1 to 3 carbon atoms; n is 0, 1 or 2; R2 and R3 are the same or different and are each hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, vinyl, allyl, propenyl, cycloalkyl of 3 to 6 carbon atoms, cycloalkenyl of 3 to 6 carbon atoms, mono-, di- or tri-halo lower alkyl or aryl; R4, r5 and R6 are the same or different and are each hydrogen, nitro, cyano, (R)2 N--, (R)2 N--CO--, R--CO--NH--, R--O--CO--, R--CO--O--, R--, R--O--, wherein R is as above defined, H2 N--SO2 --, chlorine, bromine, iodine, fluorine or trifluoromethyl; G is hydrogen or straight or branched chain alkyl of 1 to 5 carbon atoms; and B is a moiety of the formula SPC6 wherein R7, r8 ad R9 are the same or different and are each hydrogen, halogen, nitro, hydroxy, R--, R--0--, R--S--, R--SO--, R--SO2 --, (R)2 N--, R--CO--NH--, or R--CO--O--, wherein R is as above defined; the arrow in the divalent linking group → means that the linkage of two atoms by the free valencies of his group must take place as indicated by the arrow; exhibit activity against both Gram-positive and Gram-negative bacteria.

Penicillins

Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the α-carbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamido or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.

Penicillins

Penicillins of the formula EQU1 or pharmaceutically acceptable non-toxic salts thereof, wherein C* is a carbon atom constituting a center of chirality; A is a moiety of the formula EQU2 or EQU3 wherein X is EQU4 Y is EQU5 or wherein Aryl is an aryl moiety; Z is EQU6 Q1 is EQU7 or SPC1 Q2 is EQU8 SPC2 or SPC3 R is straight- chain or branched alkyl of 1 to 5 carbon atoms; R1 is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkenyl of 3 to 10 carbon atoms. vinyl, arylvinyl, mono-, di-, or tri-halo-lower alkyl, H2 N--, R--NH--, (R)2 N--, aryl--NH--, aryl-lower alkylamino, alkoxy of 1 to 8 carbon atoms, aralkoxy of 1 to 8 carbon atoms in the alkoxy portion, cycloalkoxy of 3 to 7 carbon atoms, aryloxy, R--O--V--, R--S--V--, N=C--V--, R--O--CO--V--, H2 N--CO--V--, R--NH--CO--V--, R--O--CO--NH--, R--SO2 --NH--, (R)2 N--CO--V--, wherein R is as above defined, SPC4 SPC5 provided that when X is --SO2 --, R1 is not alkoxy, aralkoxy, cycloalkoxy or aryloxy, and further provided that R1 can also be hydrogen when X is --CO--; V is a divalent organic radical of 1 to 3 carbon atoms; n is 0, 1 or 2; R2 and R3 are the same or different and are each hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, vinyl, allyl, propenyl, cycloalkyl of 3 to 6 carbon atoms, cycloalkenyl of 3 to 6 carbon atoms, mono-, di- or tri-halo lower alkyl or aryl; R4, r5 and R6 are the same or different and are each hydrogen, nitro, cyano, (R)2 N--, (R)2 N--CO--, R--CO--NH--, R--O--CO--, R--CO--O--, R--, R--O--, wherein R is as above defined, H2 N--SO2 --, chlorine, bromine, iodine, fluorine or trifluoromethyl; G is hydrogen or straight or branched chain alkyl of 1 to 5 carbon atoms; and B is a moiety of the formula SPC6 wherein R7, r8 and R9 are the same or different and are each hydrogen, halogen, nitro, hydroxy, R--, R--O--, R--S--, R--SO-- , R--SO2 --, (R)2 N--, R--CO--NH--, or R--CO--O-- , wherein R is as above defined; the arrow in the divalent linking group ←Q2 → means that the linkage of two atoms by the free valencies of this group must take place as indicated by the arrow; exhibit activity against both Gram-positive and Gram-negative bacteria.

Penicillins

Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the α-carbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamide or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.