Alkanamides

Separation and purification of Af-substituted-(indol-3-yl)-carboxamides and alkanamides... 

Nitrobenzoylamino)-2,2-dimethylpropanamide (143 R = Me) reacts in methanol-DMSO solution with sodium methoxide to yield 5,5-dimethyl-2-(4-nitrophenyl)imidazol-4(5//)-one (144 R = Me). The 4-methoxyphenyl derivative and the parent phenyl derivative react similarly, as do compounds in which variation of the 2-substitutent (R = Pr , Ph, 4-O2NC6H4) was made. The mechanism of the cyclization probably involves initial formation of the anion of the alkanamide (145), which adds to the carbonyl group of the benzamido moiety to yield the tetrahedral oxyanion (146) proton transfer and dehydration then yield the heterocycle (144). The kinetics of hydrolysis in water at 70 °C and pH 2-11 of A-glycidylmorpholine (147) have been reported. ... 

A solution of 100 mmol of the undistilled, crude /V-methyl-2-(2,2-dimelhylpropy]ideneamino)alkanamide 6 (R1 = CH3) in 30 ml of methanol is added a I 0 C to 60 mL of methanol saturated with hydrogen chloride. After 0.5 h at 0 eC, the solution is stirred at 20 °C for 2 h and then concentrated under water pump vacuum. Prepared in this way are ... 

An interesting selectivity, that appears to be fairly general, is observed in the catalytic hydrogenation of 2-fluoro-2-nitroalkanoates and -alkanamides 15 and 17, respectively. Both substituents are reduced in the esters, while in the amides only fluorine is replaced, despite using various catalysts. The parent functional group remains untouched in all of the reductions. 140... 

The naming of amides is summarized in Section 7-7D. The points to remember are that they generally are named either as (i) alkanamides, in which the prefix alkan(e) is determined by the longest carbon chain that includes the... 

R)ArLi / UAIH4 or BH3-SMe2 or NaBH4-CF3C02H (alkanamide, 4- and 5-alkanelactams)... 

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