Name | UREA, N-(2,6-DIMETHYLPHENYL)-N'-[IMINO(METHYLAMINO)METHYL]- |
Synonyms | Smodin Lidarral WHR-1142A Lidamidine N-(2,6-Dimethylphenyl)-N'-[imino(methylamino)methyl]urea UREA, N-(2,6-DIMETHYLPHENYL)-N'-[IMINO(METHYLAMINO)METHYL]- |
CAS | 66871-56-5 |
Molecular Formula | C11H16N4O |
Molar Mass | 220.27 |
Storage Condition | 2-8℃ |
Physical and Chemical Properties | Chemical properties white powder, melting point 194~197 ℃. UV maximum absorption (water):262,271nm(ε626,524). Solubility at 25 ℃ (mg/ml): water 153.55, methanol 297.94, ethanol 88.55, chloroform 4.62, hexane 0.01. Acute toxicity LD50 male mice, male rats, female rats (mg/kg):260,267,160 oral. Acute toxic LD50 mice (mg/kg):56 intravenous injection. |
Use | Use of high-efficiency antidiarrheal drugs, mainly to inhibit intestinal secretion, and also inhibit intestinal movement. It is used for chronic diarrhea or fulminant diarrhea caused by colitis, segmental ileitis, ulcerative colitis and ulcerative proctitis, diarrhea caused by gastrointestinal dyskinesia or cancer, and diabetic diarrhea. |
Raw Materials | Sodium hydroxide Aniline 2,6-Dimethylphenyl isocyanate |
Method 1:2, 6-dimethyl-N-alkoxycarbonylaniline and free methyl guanidine (derived from methyl guanidine sulfate) react under the action of sodium hydroxide, namely delidamidine.
Method 2:122.1g(0.5 mo1) methyl guanidine sulfate was suspended in 750ml tetrahydrofuran, 80.0g(1.0 mo1)50% sodium hydroxide aqueous solution was added, and stirred for 1h. Add 50.0g of solid anhydrous sodium sulfate and stir for 0.5h. Under rapid stirring, 73.5g(0.5 mo1) isocyanic acid (2,6-dimethylphenyl ester) was added dropwise in 200ml of tetrahydrofuran solution and stirred overnight. Filtration, filtrate reduced pressure concentration. The remainder is diluted with about 1L of water, the insoluble solids are filtered out, and washed thoroughly with water. The solid is dissolved in methanol and dried with anhydrous sodium sulfate. Filtration, the filtrate is acidified with a methanol solution of saturated hydrogen chloride. Concentrate under reduced pressure, grind the residue finely, impregnate with ether. The solid was filtered out, washed with ether, and dried at 80 ℃ for 2h to obtain 114.2g of ritamidine hydrochloride with 89% yield and melting point of 194~196 ℃.
Method 3: Under the action of caustic soda, isocyanic acid (2, 6-dimethylphenyl ester) and S-methyl isothiourea reacted with methylamine to obtain Ridamidine.