Sodium acetamide benzamide

More correct ideas about the polymerization came out after the observation was made, that the polymerization induced by sodium caprolactam starts with a characteristic induction period (67, 68). Beginning with a practically zero rate, the polymerization goes on with increasing velocity up to a maximal value (curve A on fig. I). The induction period indicates that certain active groups are formed by an independent process. The previous assumption of a disproportionation reaction adopted by Hanford and Joyce (42) can be supported by model reactions like the disproportionation of acetamide, benzamide (24, 57) or N-butylacetamide (68) in the presence of the respective sodium salts. 

Place 45 g. of benzamide (Section IV, 188) and 80 g. of phosphorus pentoxide in a 250 ml. Claisen flask (for exact experimeutal details on the handling and weighing out of phosphoric oxide, see under Acetamide, Section 111,111). Mix well. Arrange for distillation (Fig.//, 29, 1 or Fig. II, 20, 1) under reduced pressure use a water pump with an air leak in the system so that a pressure of about 100 mm. is attained. Heat the flask with a free flame until no more liquid distils the nitrile will pass over at 126-130°/100 mm. Wash the distillate with a little sodium carbonate solution, then with water, and dry over anhydrous calcium chloride or magnesium sulphate. Distil under normal pressure (Fig. II, 13, 2 or II, 13, 6) from a 50 ml. flask the benzonitrile passes over as a colourless liquid at 188-189° (compare Section IV,66). The yield is 28 g. 

Reduction to Amines. Place 100 mg of the unknown in a reaction tube, add 0.2 g of tin, and then—in portions—2 mL of 10% hydrochloric acid. Reflux for 30 min, add 1 mL of water, then add slowly, with good cooling, sufficient 40% sodium hydroxide solution to dissolve the tin hydroxide. Extract the reaction mixture with three 1-mL portions of ether, dry the ether extract over anhydrous sodium sulfate, wash the drying agent with ether, and evaporate the ether to leave the amine. Determine the boiling point or melting point of the amine and then convert it into a benzamide or acetamide as described under 4. Primary and Secondary Amines p. 587. 

E) Hydrolysis of Amides. Place in a test tube 0.5 g of acetamide and add 3 ml of sodium hydroxide solution. Boil and note the odor. Repeat, using 5 ml of dilute sulfuric acid and 0.5 g of benzamide. Boil for a few minutes and notice any change. 

The final conditions were scaled up with no problems chalcone 8a and guanidine (liberated from its hydrochloride with sodium ethoxide) were heated in dimethyl acetamide while bubbling air through the mixture to form pyrimidine 9a. After complete conversion (16 h), the product was cleaved from the support (20% trifluoroacetic acid in DCM). Pure 4-(2-amino-6-phenyl-pyrimidin-4-yl)benzamide 1 was obtained as its trifluoroacetate salt upon evaporation of the filtrate and recrystallisation of the residue from ethanol/water in 56% overall yield based on the solid phase attached 4-carboxybenzaldehyde 6a. 

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