Product Name

  • Name

    Cefazedone

  • EINECS 264-293-9
  • CAS No. 56187-47-4
  • Article Data8
  • CAS DataBase
  • Density 1.78 g/cm3
  • Solubility
  • Melting Point
  • Formula C18H15Cl2N5O5S3
  • Boiling Point
  • Molecular Weight 548.452
  • Flash Point
  • Transport Information 5kgs
  • Appearance White to yellowish white powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 56187-47-4 (Cefazedone)
  • Hazard Symbols
  • Synonyms 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(3,5-dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-,(6R,7R)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(3,5-dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-,(6R-trans)-;Cefazedone;Refosporen;
  • PSA 213.33000
  • LogP 2.17470

Synthetic route

C12H13Cl2NO4

C12H13Cl2NO4

C11H12N4O3S3*ClH

C11H12N4O3S3*ClH

cefazedone
56187-47-4

cefazedone

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 5℃; for 0.5h; pH=6.8;95%
C15H12BrCl2N3O5S

C15H12BrCl2N3O5S

2-mercapto-5-methyl-1,3,4-thiadiazole
29490-19-5

2-mercapto-5-methyl-1,3,4-thiadiazole

cefazedone
56187-47-4

cefazedone

Conditions
ConditionsYield
With triethylamine In ethanol for 10h; Solvent; Reagent/catalyst; Reflux;93.86%
2-(3,5-dichloro-4-oxopyridine-1(4H)-yl)acetic acid
56187-37-2

2-(3,5-dichloro-4-oxopyridine-1(4H)-yl)acetic acid

(6R,7R)-7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
30246-33-4

(6R,7R)-7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

cefazedone
56187-47-4

cefazedone

Conditions
ConditionsYield
With ortho-iodophenylboronic acid In toluene Solvent; Reflux;93%
(i) SOCl2, DMF, (ii) /BRN= 629621/, Et3N, CH2Cl2; Multistep reaction;
2-(3,5-dichloro-4-oxopyridine-1(4H)-yl)acetic acid
56187-37-2

2-(3,5-dichloro-4-oxopyridine-1(4H)-yl)acetic acid

cefazedone
56187-47-4

cefazedone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1,3,5-trichloro-2,4,6-triazine; triethylamine / N,N-dimethyl-formamide / 1.33 h / Cooling with ice
1.2: 1.75 h / 20 °C
2.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux
3.1: triethylamine / ethanol / 10 h / Reflux
View Scheme
3-deacetyloxy-7-aminocephalosporanic acid
22252-43-3, 26395-99-3, 70287-30-8, 72059-35-9

3-deacetyloxy-7-aminocephalosporanic acid

cefazedone
56187-47-4

cefazedone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1,3,5-trichloro-2,4,6-triazine; triethylamine / N,N-dimethyl-formamide / 1.33 h / Cooling with ice
1.2: 1.75 h / 20 °C
2.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux
3.1: triethylamine / ethanol / 10 h / Reflux
View Scheme
7-Aminocephalosporanic acid
957-68-6

7-Aminocephalosporanic acid

cefazedone
56187-47-4

cefazedone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate; acetic acid / 5 - 10 °C
2: triethylamine / acetonitrile / 0.5 h / 0 - 5 °C / pH 6.8
View Scheme
cefazedone
56187-47-4

cefazedone

(6R,7R)-3-[[(5-methyl-1,3,4-thiadiazolyl-2-yl)thio]methyl]-7-[2-(3,5-dichloro-4-pyridone-1-acetylamido)]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt
63521-15-3

(6R,7R)-3-[[(5-methyl-1,3,4-thiadiazolyl-2-yl)thio]methyl]-7-[2-(3,5-dichloro-4-pyridone-1-acetylamido)]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt

Conditions
ConditionsYield
Stage #1: cefazedone With triethylamine In methanol at 0 - 10℃; for 0.5h;
Stage #2: With sodium 2-ethylhexanoic acid In methanol; acetone at 0 - 10℃; for 3.5h;		95.2%
Stage #1: cefazedone With triethylamine In methanol at 0 - 10℃; for 0.5h;
Stage #2: With sodium 2-ethylhexanoic acid In acetone at 0 - 10℃; for 3.5h;		95.2%

Cefazedone Specification

The Cefazedone with the CAS number 56187-47-4 is also called 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[2-(3,5-dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-,(6R,7R)-. The IUPAC name is (6R,7R)-7-[[2-(3,5-dichloro-4-oxopyridin-1-yl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Its molecular formula is C18H15Cl2N5O5S3.

The properties of the chemical are: (1)ACD/LogP: 0.92; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -1.96; (4)ACD/LogD (pH 7.4): -2.79; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 10; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 191.85 Å2; (13)Index of Refraction: 1.76; (14)Molar Refractivity: 126.33 cm3; (15)Molar Volume: 306.7 cm3; (16)Polarizability: 50.08×10-24cm3; (17)Surface Tension: 102.2 dyne/cm.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CN/3/C=C(/Cl)C(=O)C(\Cl)=C\3)CSc4nnc(s4)C)C(=O)O
(2)InChI: InChI=1/C18H15Cl2N5O5S3/c1-7-22-23-18(33-7)32-6-8-5-31-16-12(15(28)25(16)13(8)17(29)30)21-11(26)4-24-2-9(19)14(27)10(20)3-24/h2-3,12,16H,4-6H2,1H3,(H,21,26)(H,29,30)/t12-,16-/m1/s1
(3)InChIKey: VTLCNEGVSVJLDN-MLGOLLRUBC

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