Acetamide from ethyl acetate

Succinamide. Add 5 g. (4-8 ml.) of dimethyl succinate to 25 ml. of concentrated ammonia solution (sp. gr. 0-88) in a 100 ml. conical flask. Cork the flask and shake the contents for a few minutes aUow to stand for 24 hours with occasional shaking. Filter off the crystals of succinamide, and wash with a Uttle cold water. RecrystaUise from a little hot water. Dry in the steam oven and determine the m.p. The yield is 3-5 g. Pure succinamide melts at 254° with decomposition. 

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Preparation of Acetamide from Ethyl Acetate (SECTION 221).—Mix in a 250-cc. distilling flask 50 grams of ethyl acetate and 100 cc. of a concentrated aqueous solution of ammonia... 

Synthesis of Acetamide from Ethyl Acetate and Ammonia... 

N- -Propyl-3-thiophen-2-yl-acetamide. To a solution of -propylamine (5.9 g, 100 mmol) in dichloromethane (50 mL) and 2N NaOH (10 mL) was added dropwise 3-thienylacetyl chloride 46 (2.8 g, 17.4 mmol) dissolved in dichloromethane (10 mL). The reaction mixture was stirred for 2h at RT. The two layers were separated and the aqueous layer was extracted with dichloromethane (20 mL). The combined organic layers were washed with brine, dried over Na2S04 and concentrated under reduced pressure to yield 2.3 g (72 %) oil which solidified upon standing which was recrystallized from ethyl acetate-hexane JH NMR (CDC13) 8 0.8 (t, 3H, J =... 

Acetamide [60-35-5] M 59.1, m 81 , pK -1.4, pKl +0.37. Crystd by soln in hot MeOH (0.8mL7g), diltd with Et20 and allowed to stand [Wagner J Chem Educ 7 1135 1930]. Alternate cry sms are from acetone, benzene, chloroform, dioxane, methyl acetate or from benzene-ethyl acetate mixture (3 1 and 1 1). It has also been recrystd from hot water after treating with HCl-washed activated charcoal (which had been... 

Secondary nitramines are conveniently prepared from the nitrolysis of A, A-dialkylamides with nitronium salts in acetonitrile or ethyl acetate at 20 °C where the acyl group is converted into an acylium tetrafluoroborate (Equation 5.14). Problems can occur if commercial nitronium salts like the tetrafluoroborate are used without purification. The presence of nitrosonium salts can then lead to nitrosamines via nitrosolysis. Yields of secondary nitramine up to 90 % have been reported with solutions of nitronium tetrafluoroborate in acetonitrile di-n-butylnitramine is obtained in 82 % yield from the nitrolysis of corresponding acetamide. ... 

A typical example that illustrates the method concerns the lipase- or esterase-catalyzed hydrolytic kinetic resolution of rac-1-phenyl ethyl acetate, derived from rac-1-phenyl ethanol (20). However, the acetate of any chiral alcohol or the acetamide of any chiral amine can be used. A 1 1 mixture of labeled and non-labeled compounds (S)- C-19 and (f )-19 is prepared, which simulates a racemate. It is used in the actual catalytic hydrolytic kinetic resolution, which affords a mixture of true enantiomers (5)-20 and (J )-20 as well as labeled and non-labeled acetic acid C-21 and 21, respectively, together with non-reacted starting esters 19. At 50% conversion (or at any other point of the kinetic resolution), the ratio of (5)- C-19 to (1 )-19 correlates with the enantiomeric purity of the non-reacted ester, and the ratio of C-21 to 21 reveals the relative amounts of (5)-20 and (J )-20 (98). 

The thioureido-acetamide lb (2.00 mmol) and 2 (2.00 mmol) were weighed into a 10-mL ball-mill vessel. The mixture became immediately solid and was ball-milled at 25 Hz for 1 h. 3b remained insoluble in hot ethyl acetate whereas 4b dissolved and was separated by filtration. 3b was recrystallized from DMSO (3b, yield 54%). The ethyl acetate extract was evaporated to dryness and the crude solid recrystallized from ethanol (4b, yield 26%). 

Benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate (2.29 g) was treated with bis(trimethylsilyl)acetamide (4.06 ml) at room temperature for 50 min to give a clear solution. Top the solution was added an acid chloride solution, which was prepared from (Z)-2-hydroxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (2.04 g) and PCI5 (1.15 g) in methylene chloride (20 ml). The mixture was stirred at room temperature for 30 min, poured in cold water (200 ml) and extracted with ethyl acetate (100 ml x 3). After evaporation of the solution was obtained the syrup (4 g) which was chromatographed on a silica gel column by eluting with 10 1 and 3 1 mixture of toluene and ethyl acetate successively. After evaporation of the solvents was obtained benzhydryl 3-chloromethyl-7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (2.62 g, 68%). 

Pyridinium dichromate, prepared from chromium trioxide in a minimum amount of water and pyridine, forms a bright-orange solid and is soluble in water, dimethylformamide, dimethyl sulfoxide, and dimethyl-acetamide sparingly soluble in dichloromethane, chloroform, and acetone and almost insoluble in hexane, toluene, ether, and ethyl acetate. Allylic secondary alcohols are oxidized more rapidly than their saturated analogues. Oxidations are carried out in dichloromethane solutions at 25 °C, and ketones are obtained in high yields (equation 251) [603. ... 

The crude acetamide may be recrystallized from a mixture of three parts of benzene to one part of ethyl acetate, or from an alcohol-ether mixture. Dissolve 0.5 g of acetamide in 1 ml of methanol by warming cool, and add 6-7 ml of ether. Cork tube, and cool. If crystals do not separate within a few minutes, even on stirring, add a minute crystal of pure acetamide and allow to stand. Filter the crystals with suction and wash with ether. Place on a paper disc or watch glass and dry in a dessicator. Determine the melting point. 

Yellow needles from ale, mp 312° (dec). Sublimes above 310°. Moderately sol in boiling nitrobenzene sparingly sol in boiling ale. somewhat more sol in a mixture of glacial acetic acid and nitric acid. Practically insol in acetone, chloroform, benzene, dioxane. acetic acid, ether and linseed Oil-Solubilities in g/100 ml solvent at 25° watet 2 x I0 ethanol 0.007 ethyl acetate 0.015 petr ether 0.0 xylene <0.01 methyl Cellosolve 0.1 dimethyl acetamide 0.14 dimethyl sulfoxide 0.47. 

Acetamide may be most conveniently prepared by allowing a mixture of one volume of ethyl acetate and two volumes of concentrated ammonia to stand until a homogeneous solution is formed. The amide is obtained from the aqueous solution by distillation. The reaction which takes place is an example of a general reaction made use of in the preparation of other amides —... 

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