N4-Benzoylcytosine Chemical Properties

Melting point:

>300 °C (dec.) (lit.)

Density 

1.33±0.1 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Aqueous Acid (Slightly, Heated), DMSO+DCl (Slightly, Heated)

form 

Solid

pka

7.75±0.10(Predicted)

color 

Off-White

InChI

InChI=1S/C11H9N3O2/c15-10(8-4-2-1-3-5-8)13-9-6-7-12-11(16)14-9/h1-7H,(H2,12,13,14,15,16)

InChIKey

XBDUZBHKKUFFRH-UHFFFAOYSA-N

SMILES

C(NC1=CC=NC(=O)N1)(=O)C1=CC=CC=C1

Surface tension

72.2mN/m at 1g/L and 21.2℃

CAS DataBase Reference

26661-13-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich

N4-Benzoylcytosine Usage And Synthesis

Chemical Properties

White or almost white crystalline powder

Uses

N⁴-Benzoylcytosine may be employed for the following syntheses:

• 3′-C-ethynyl and 3′-C-(1,4-disubstituted-1,2,3-triazolo) double-headed pyranonucleosides
• 2′-C-methyl-4′-thiocytidine, via the Pummerer reaction
• 2′-fluorinated L-nucleoside analogs

Uses

N4-Benzoylcytosine is a reactant in the synthesis of 1'',2''-cyclopentyl nucleosides as potential antiviral agents.

General Description

N⁴-Benzoylcytosine is an amide and its anti-microbial activity against pathogenic microorganisms has been studied using the Disk Diffusion and the Pour Plate method. It can be synthesized via the condensation of benzoyl chloride with cytosine.

Synthesis

Under nitrogen protection, 100 L of acetonitrile was added to the reactor as a solvent, followed by 22 kg (196 mol) of 6-aminopyrimidin-2(1H)-one (anhydrous cytosine), 25 g of 4-dimethylaminopyridine (DMAP), and 24 kg of triethylamine as a base. After cooling the reaction mixture to 5-8°C, 34 kg of benzoyl chloride was slowly added dropwise. After the dropwise addition, the reaction mixture was allowed to warm up naturally to room temperature and stirred at 25°C for 1 hour. Subsequently, the reaction mixture was slowly heated to 40-45°C and kept at this temperature for 2 hours. Upon completion of the reaction, it was cooled to room temperature and press-filtered. About 60 L of acetonitrile filtrate was collected for recycling, and the filter cake was washed sequentially with water and ethanol, and dried to give 40 kg of a white solid product, N4-benzoylcytosine, which was analyzed by liquid chromatography to be 99.2% pure.

References

[1] Patent: US2011/245458, 2011, A1
[2] Chemical Communications, 2017, vol. 53, # 64, p. 8952 - 8955
[3] Heterocyclic Communications, 2007, vol. 13, # 4, p. 251 - 256
[4] Russian Journal of Organic Chemistry, 2008, vol. 44, # 3, p. 358 - 361
[5] Journal of the Chemical Society, 1956, p. 2388,2392

N4-Benzoylcytosine(26661-13-2)Related Product Information

• Sodium benzoate
• Benzamide
• Cytosine
• Chlorantraniliprole
• Fluorocytosine
• Dihydromyrcenol
• Propanamide, N-(6,7-dihydro-6-oxo-1H-purin-2-yl)-2-methyl-
• N-ALLYLBENZYLAMINE
• N-Allylmethylamine
• 3-Pyridinecarboxamide, 5-chloro-N-methyl-
• 2'-deoxy-2'-fluoro-2'-C-methylcytidine
• 2'-C-Methyl-, 2',3',5'-tribenzoateuridine
• (2R)-2-Deoxy-2-fluoro-2-Methyl-D-erythro-pentonic acid-g-lactone 3,5-bis(4-chlorobenzoate)
• ((2R,3S,4S)-3-(benzoyloxy)-4-fluoro-4-Methyl-5-oxotetrahydrofuran-2-yl)Methyl benzoate
• 3-Pyridinecarboxamide, 4-chloro-N-methyl-
• 4-Pyridinecarboxamide, 3-chloro-N-methyl-
• (3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxyMethyl)-3-Methyl-dihydrofuran-2(3H)-one
• 5'-O-Dimethoxytrityl-N-benzoyl-desoxycytidine