Réaction #5864

Équation de réaction

ammonium acetate

N,α-bis-formyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl) glycine methyl ester

ammonium acetate

acetic acid

→

1-(1,2,3,4-tetrahydronaphthalen-1-yl) -5-imidazolecarboxylic acid methyl ester

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températureare refluxed for 8 hours
2. 2
   Extractionextracted twice, with 100 ml of toluene each time
3. 3
   Concentrationconcentrated
4. 4
   Autreseparated at silica gel by chromatography

Mode opératoire

A mixture of 16.5 g of N,α-bis-formyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl) glycine methyl ester, 65.0 g of ammonium acetate and 100 ml of acetic acid are refluxed for 8 hours. Then additional 50 g ammonium acetate are added and the refluxing is continued for further 4 hours. The solution is diluted with 300 ml of water and extracted twice, with 100 ml of toluene each time. The organic phases are combined, concentrated and separated at silica gel by chromatography. Concentration of the eluate yields 1-(1,2,3,4-tetrahydronaphthalen-1-yl) -5-imidazolecarboxylic acid methyl ester, having a melting point of 63° C.

Source