Staab, Heinz A.’s team published research in Chemische Berichte in 95 | CAS: 360-92-9

Chemische Berichte published new progress about 360-92-9. 360-92-9 belongs to amides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain,Amide, name is N,N-Diethyl-2,2,2-trifluoroacetamide, and the molecular formula is C10H15ClO3S, Name: N,N-Diethyl-2,2,2-trifluoroacetamide.

Staab, Heinz A. published the artcileN-Trifluoroacetyl- and N-trichloroacetylimidazole, Name: N,N-Diethyl-2,2,2-trifluoroacetamide, the publication is Chemische Berichte (1962), 2070-2, database is CAplus.

The syntheses and reactions of N-trifluoroacetylimidazole (I) and N-trichloroacetylimidazole (II) are described. N,N’-Carbonyldiimidazole (III) (20.5 g.) in 100 cc. dry THF treated dropwise with 28.8 g. CF3CO2H in 80 cc. THF, cooled several hrs., and filtered gave imidazolium trifluoroacetate (IV), m. 136-7° (tetrahydrofuran); distillation of the filtrate yielded 14.4 g. I, b14 45-6°. Imidazole (V) (25.8 g.) in 120 cc. dry THF treated dropwise with cooling with 39.9 g. (CF3CO)2O in 50 cc. THF, filtered from the IV, and distilled gave 24.8 g. I. CCl3CO2H (39.1 g.) and 19.5 g. III in C6H6 gave in the usual manner imidazolium trichloroacetate (VI), m. 93-4.5° (decomposition) (CHCl3), and from the filtrate 18.5 g. II, b0.001 60-2°, m. 38.5-40°. (CCl3CO)2O (31.3 g.) added dropwise with cooling to 17.8 g. V in 170 cc. C6H6, filtered from the VI, and distilled yielded 21.7 g. II. I treated in Et2O or THF at room temperature with an equivalent amount of an appropriate alc. gave the following CF3CO2R (R, % yield, m.p. or b.p./mm., and n20D given): cyclohexyl, 73, 148-9°/760, 1.3839; iso-Am, 74, 119-20°/760, 1.3513; Me3C, 73, 83°/760, 1.3302 (at 25°); Ph, 75, 48-9°/16, 1.4187 (at 25°). II gave similarly the following CCl3CO2R (same data given): cyclohexyl, 81, 122.5-3.5°/14, 1.4805; iso-Am, 84, 97.5-98°/15, 1.4520; Me3C, 78, 25-6°, -; Ph, 79, 124.5-25°/14, 1.5253. I treated at room temperature with an equivalent amount of an appropriate amine in THF or Et2O and evaporated, and the residue washed with H2O gave the corresponding amides of CF3CO2H (% yield, and m.p. or b.p./mm. given): diethylamide, 74, 157-8°/760; anilide, 83, 89-90°; 2-naphthylamide, 83, 146-7.5°; p-nitranilide, 84, 151-3°; carbethoxymethylamide, 51, 51°. II gave similarly the following amides of CCl3CO2H (same data given): diethylamide, 82, 26-7°; anilide, 90, 94.5-5.5°; N-methylanilide, 87, 72-2.5°. p-H2NC6H4CO2H (4.12 g.) and 10 g. I in Et2O at room temperature gave 5.5 g. p-CF3CONHC6H4CO2H (VII), m. 284-5° with resolidification to a solid which does not melt up to 350°. A similar run with equivalent amounts of reactants gave only 38% VII. VII heated 1 h. at 300° gave with the elimination of CF3CO2H a polyamide of p-H2NC6H4CO2H.

Chemische Berichte published new progress about 360-92-9. 360-92-9 belongs to amides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain,Amide, name is N,N-Diethyl-2,2,2-trifluoroacetamide, and the molecular formula is C10H15ClO3S, Name: N,N-Diethyl-2,2,2-trifluoroacetamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics