Acetyl chloride acetamide from

In other respects, benzoyl chloride is a wholly normal add-chloride, and what was said under acetyl chloride is applicable to this chloride only it is possible to prepare aromatic amides by a different method from that used for the preparation of acetamide-... 

Dihydroxypyrrolidinones, which can be considered as cyclic GABA derivatives, are potential nootropic drug candidates. All four possible diastereomers 794—797, as shown in Scheme 174, can be prepared from tartaric acid. Treating L-tartaric acid sequentially with acetyl chloride, methyl glycinate, and then acetyl chloride provides in 81% overall yield the C2-symmetric succinimide 790. In order not to reduce the methyl ester, the very mild treatment with sodium borohydride at —40 °C is employed to prepare the cw-hydroxylactam 791 in an 80% isolated yield. Esterification of 791 with trifiuoroacetic anhydride followed by triethylsilane reduction yields to the extent of 79% the pyrrolidinone 792. This is deprotected with sodium methoxide to provide in 97% yield (3i ,45)-3,4-dihydroxy-A -methoxy-carbonylmethyl-2-pyrrolidinone (793). Ammonolysis of 793 affords (3i ,4 S)-3,4-dihydroxy-2-oxopyrrolidine-A -acetamide (794) in 60% yield. Subsequent modifications to 793 allow for the preparation of (35, 4S)-3,4-dihydroxy-2-oxopyrrolidine-A/-acetamide (795), (3R,4R)-3,4-dihydroxy-2-oxopyrrolidine-A -acetamide (796) and (35, 47 )-3,4-dihydroxy-2-oxopyrrolidine-7V-acetamide (797) [234]. 

Acetyl chloride added dropwise with stirring to a soln. of diethyl iminocarbonate and 1 eq. NEt3 in carbon tetrachloride at 0°, and stirring continued at room temp, for 24 h N-(diethoxymethylene)acetamide. Y 71 %. F.e., also diaryl esters from N-acylimino-carbonyl chlorides and phenols, s. E.-U. Wiirthwein et al., Chem. Ber. 121, 991-8 (1988). 

Sulfonyl fluorides are readily obtained from sulfonyl chlorides and KF or KHF2j even in an aqueous medium.801"804 Carboxylic acid fluorides are formed when the acid chlorides are heated with dry KF and can be removed continuously from the reaction mixture by distillation through a column formyl and acetyl fluorides are thus obtained when the acid is heated with benzoyl chloride and KF.805,806 Xylene or acetamide may be used as diluent. Further, a>chloro and at-bromo fatty esters, nitriles, and amides react with KF at temperatures around 100-150°. 

The Bischler-Napieralski synthesis of l-methyl-3,4-dihydroisoquinoline (18) from N-(2-phenylethyl)acetamide (19) in the presence of heat and acid (72) was not predicted by the Electrophilic Aromatic module of CAMEO this module of CAMEO predicted instead the formation of methyl 2-acetyl-phenethylamine, 20 (Scheme 5). In a related case, CAMEO predicted (when the Electrophilic Aromatic module was chosen) that 4-anilino-butan-2-one (21) would undergo intramolecular cyclization to form 4-hydroxy-4-methyl-tetrahydroquinoline, 23 (Scheme 6). Apparently, CAMEO correcdy perceives the eneamine character of 21 as necessary for this reaction to occur. It was noted in this case that ring formation, as predicted by CAMEO, depended upon the presence of mineral acid, but did not occur if a Lewis acid (e.g., stannic chloride) was selected instead as the reagent. It is known, however, that intramolecular cyclization of 21 does occur in the presence of a Lewis acid and yields 4-methyl-quinoline, 22, as product (74). 

The 2-acetoxyimino-2-deoxy- glycosyl azide 62 was obtained from the corresponding a-chloride (by reaction with NaNj, CH3CN), and converted into the (V-(2-deoxy-2-oximino-p-gIycosyI)-acetamide 63 in low yield on hydrogenation (Scheme 4). 0- N Acetyl migration was a... 

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