Chloracetanilide

Bei der, Umlagerung" von N-Chloracetanilid mit radioaktivem Chlor als Katalysator fanden Olson, Halford und Hornel 149) eine voll-standige Gleichverteilung der Radioaktivitat mit dem Chlor, das in die o- bzw. p-Stellung in den Kern eintritt. Daraus kann auf einen inter-molekularen ionogenen Reaktionsmechanismus geschlossen werden,... 

Chloracetanilide herbicides like alachlor, metolachlor and metazachlor can be analysed in positive-ion mode. In ESI, protonated and sodiated molecules are observed as well as the loss of methanol [16, 34, 47, 63]. The MS-MS spectmm of alachlor was stndied, nsing MS-MS and in-source CID on a orthogonal-acceleration time-of-flight mass spectrometer [63]. 

As an example 2.5 1 of estuarine water were extracted with two times 100 ml dichloromethane for the analysis of chloracetanilide, triazine, and phenylurea herbicides. The extract was evaporated to dryness and the residue was dissolved in 400 pi of methanol, from which 10 pi was injected in LC-MS. Typical absolute detection hmits in SIM are between 10 and 500 pg [74]. 

A variety of neutral degradation products of the chloracetanilide herbicide alachlor was identified [63, 115]. However, the ionic metabohtes such as the oxoethanesulfonic acid derivative appear to be of more significance, as they are readily leached to groundwater. WMe alachlor itself is amenable to GC-MS, its ionic metabolites are not. Initially, GC-MS, LC-UV-DAD, and fast-atom bombardment MS-MS were applied in the analysis and identification of such metabolites [119]. Subsequently, the potential of LC-ESI-MS in this area was recognized [120]. Both oxanilic acid and oxoethanesulfonic acid metabohtes of alachlor, acetochlor and metolachlor were identified in snrface water and gronnd water, and subsequently determined with detection limits at the 0.01-pg/l level using off-hne SPE in combination with LC-MS [120]. 

Numerical Illustration.—The rate of conversion of acetochloranilide into p-chloracetanilide, just exactly four minutes after the reaction had started, was found to be 4 42 gram-molecules per minute. The time of observation was infinitely small. When the measurement occupied the whole four minutes, the average velocity was found to be 8 87 gram-molecules per minute when the measurement occupied two minutes, the average velocity was 5 90 units per minute and finally, when the time of observation occupied one minute, the reaction apparently progressed at the rate of 4-70 units per minute. Obviously then we approximate more closely to the actual velocity, 4 42 gram-molecules per minute, the smaller the time of observation. 

Synonyms 2-Chloro-6 -ethyl-N-(2-methoxy-1 -methylethyl) acet-o-toluidide a-Chloro-2 -ethyl-6 -methyl-N-(1-methyl-2-methoxyethyl)-acetanilide 2-Chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide 2-Chloro-N-(6-ethyl-o-tolyl)-N-(2-methoxy-1 -methylethylj-acetamide 2-Ethyl-6-methyl-1 -N-(2-methoxy-1 -methylethyl) chloroacetanilide Classification Chloracetanilide Empirical C1SH22CINO2... 

Eormanilides (R = H) and chloracetanilides (R = CHjCl) are used in these preparations. The formation of an Atherton-Todd product in this reaction is probably due to the high N-H acidity of formanilide and chloracetanilide. 

Some compound classes have been widely analyzed using ESI-MS, enabhng statements on the likeliness of Na+-cationizatioa Pesticide classes that are prone to the formation of [M+Na]+, often next to [M+H]+,are carbamate and oiganophos-phorus pesticides, and various classes of herbicides like phenylureas, sulfonylmeas, and chloracetanilides. Antibiotics that readily show [M+Na] next to [M+H]" are sulfonamides, betalactams, tetracychnes, aminoglycosides, and macrolides. The... 

Ketene passed 15-20 min, into stirred chloracetic acid, the resulting liquid containing the intermediate acetic chloracetic anhydride added to the calculated amount of aniline, then 1-2 ml. water added chloracetanilide. Y 78%. F. e., also isolation of the intermediate, s. Y. V. Svetkin and G. Kretsu, 28, 1864 (1958) G. A. 53, 1112d. 

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