Reaction #4258

Reaction equation

dicyclohexylcarbodiimide

1-(3-carboxyphenyl)-5-mercaptotetrazole

4-(2-formylhydrazino)aniline

→

desired compound

Yield 25.4%

5-Mercapto-1-{3-[4-(2-Formylhydrazino)Phenylcarbamoyl]Phenyl}Tetrazole

Yield 25.4%

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   OtherThe precipitated dicyclohexylurea was separated by filtration
3. 3
   workup.ADDITIONthe filtrate was added to 500 ml of ice-water
4. 4
   workup.STIRRINGwhile stirring
5. 5
   FiltrationThe thus precipitated crystals were filtered
6. 6
   Washwashed with water
7. 7
   workup.ADDITIONdispersed in 100 ml of hot methanol
8. 8
   Temperatureto cool to room temperature
9. 9
   Filtrationfiltered
10. 10
    WashThe filtrate was washed with methanol

Procedure

In 50 ml of dimethylformamide were dissolved 11.1 g of 1-(3-carboxyphenyl)-5-mercaptotetrazole and 7.6 g of 4-(2-formylhydrazino)aniline, and a solution of 10.3 g of dicyclohexylcarbodiimide in 10 ml of dimethylformamide was added dropwise to the solution at 0° C. in a nitrogeneous atmosphere over about 30 minutes. After the addition, the mixture was stirred at room temperature for 3 hours. The precipitated dicyclohexylurea was separated by filtration, and the filtrate was added to 500 ml of ice-water while stirring. The thus precipitated crystals were filtered, washed with water and dispersed in 100 ml of hot methanol. The dispersion was allowed to cool to room temperature and filtered. The filtrate was washed with methanol to obtain 4.5 g of the desired compound. Melting point: 202° C. (with decomposition).

Source