Glycine → HCID 21835782, compound

Participants

Reaction Conditions

Reaction Steps

47.8 g (0.25 mol) of 2,4-dichlorobenzoic acid, 22.5 g (0.3 mol) of glycine,1.5 g (6.8 mmol) of basic copper carbonate and 22 g (0.55 mol) of NaOH are introduced into 300 g of N,N-dimethylacetamide and heated to 80° C. 20.8 g (0.15 mol) of potassium carbonate are added, and the mixture is heated to 100° C. After 3.5 h at 100° C., the temperature is raised to 110° C., and the mixture is stirred at 110° C. for 3.5 h, during which 100 g of N,N-dimethylacetamide are added. After a further 100 g of N,N-dimethylacetamide has been added the mixture is heated at 120° C. for 2.5 h and at 140-150° C. for 2.5 h. After cooling to 80° C., 139.8 g (0.9 mol) of diethyl sulfate are added dropwise over the course of 2 h and, after stirring at 80° C. for 45 min, excess diethyl sulfate is destroyed by adding ammonia. 350 g of water are added to the reaction mixture, and the product is extracted with xylene. 352 g of xylene extract with a product content of about 0.17 g/g are obtained, corresponding to 59.8 g (84%) of ethyl N-carbethoxymethylene-4-chloroanthranilate.

Provenance & Evidence