Sulfamerazine Property

Melting point:

234-238°C

Boiling point:

519.1±52.0 °C(Predicted)

Density 

1.3364 (rough estimate)

refractive index 

1.6440 (estimate)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

pKa 2.29(H2O t = 24.0 I = 0.5 (NaCl)) (Uncertain)

color 

White to Off-White

Water Solubility 

202mg/L(20 ºC)

Merck 

14,8913

BRN 

249133

CAS DataBase Reference

127-79-7(CAS DataBase Reference)

NIST Chemistry Reference

Sulfamerazine(127-79-7)

EPA Substance Registry System

Benzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)- (127-79-7)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

WGK Germany 

2

RTECS 

WP0750000

F 

10

TSCA 

Yes

HS Code 

2935904000

Toxicity

LD50 oral in mouse: 25gm/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

Sulfamerazine Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Sulfamerazine,Lederle,US,1943

Uses

Antibacterial.This compound is a contaminant of emerging concern (CECs).

Definition

ChEBI: A sulfonamide consisting of pyrimidine with a methyl substituent at the 4-position and a 4-aminobenzenesulfonamido group at the 2-position.

Manufacturing Process

To a well agitated solution of 6.95 grams of 2-amino-6-methyl pyrimidine in 40 cc of pyridine, 15 grams of p-acetylaminobenzenesulfonyl chloride are added in small portions over a 30 minute period. The reaction mixture is then heated on a steam bath for 30 minutes, the free pyridine being then removed under reduced pressure and the residue mixed with cold water, and the latter mixture is vigorously stirred. The solid reaction product is removed by filtration and washed with cold water.
There is obtained a yield of 14 grams of crude 2-(pacetylaminobenzenesulfonamido)- 6-methyl pyrimidine, which on recrystallization from alcohol and water melts at 238° to 239°C. The crude product is hydrolyzed by suspending it in 400 cc of 2 N hydrochloric acid and warming until solution is complete. The solution is neutralized with sodium carbonate and the precipitated 2-(sulfanilamido)-6-methyl pyrimidine is removed by filtration. The latter on recrystallization from alcohol and water shows a melting point of 225° to 226°C.

Therapeutic Function

Antibacterial

Antimicrobial activity

Like all examined sulfanilamides, this drug is effective in treating infections caused by streptococci, gonococci, pneumococci, staphylococci, and also colon bacillus. Synonyms of this drug are dosulfin, polagin, romezin, and others.

General Description

Chemical structure: sulfonamide

Pharmaceutical Applications

2-Sulfonamido-4-methylpyrimidine. A component of some triple sulfa combinations. Plasma half-life is c. 24 h and protein binding c. 75%. It is less active than sulfadiazine.

Safety Profile

Moderately toxic by intravenous and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NO, and SOx,.

Synthesis

Sulfamerazine, N1 -(4-methyl-2-pyrimidinyl)sulfanilamide (33.1.12), is also synthesized in the manner described above, which is by reacting 4-acetylaminobenzenesulfonyl chloride with 2-amino-4-methylpyrimidine (33.1.10), which is in turn synthesized by the traditional scheme of synthesizing derivatives of pyrimidine. Acetoacetic ester is condensed with guanidine to give 4-methyl-2-aminopyrimidin-6-one (33.1.8). Reacting this with phosphorous oxychloride gives 4-methyl-2-amino-6-chloropyrimidine (33.1.9). The chlorine atom at C6 of the pyrimidine ring is then removed by reduction with hydrogen using a palladium on carbon catalyst. The resulting 4-methyl-2-aminopyrimidine (33.1.10) is then reacted with 4-acetylaminobenzenesulfonyl chloride to make an acetanilide derivative (33.1.11), the subsequent hydrolysis of which with base leads to the formation of the desired sulfamerazine.