Journal of Organic Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Formula: C3H9ClOS.
Izzo, Patrick T. published the artcilePreparation of 1-aryl-1,2-cyclopropanedicarboximides. An application of dimethylsulfoxonium methylide, Formula: C3H9ClOS, the publication is Journal of Organic Chemistry (1963), 1713-15, database is CAplus.
1-Aryl-1,2-cyclopropanedicarboximides (I) were prepared in the presence of dimethylsulfoxonium methylide (II). Trimethylsulfoxonium chloride (III) was prepared by the method of Kuhn and Trischmann (CA 52, 14523g),m. 215-16°. III(1.5g.) added to a suspension of 0.29 g. NaH in 150 ml. tetrahydrofuran (THF), the mixture refluxed with evolution of H, stirred under reflux 45-60 min., and 0.012 mole N-methyl-2-arylmaleimide added to the solution (containing II), the mixture refluxed 2 hrs., cooled, alc. added, solvent removed in vacuo, the residue taken up in CH2Cl2, and the solution washed, dried, and evaporated gave I (R, R1, m.p., % yield given): Ph, H, 55-7°, 21; Ph, Et, 113-146deg;, 81; 3,4,5-trimethoxyphenyl, H, 136-86°, 21. The structure of I was supported by infrared and ultraviolet spectra, elementary analyses, and unsaturation tests. N-Methyl-2-phenylsuccinimide (37.8 g.), 39.2 g. N-bromosuccinimide, 0.4 g. Bz2O2, and 800 ml. CCl4 refluxed 24 hrs., stored 16 hrs. at room temperature, the succinimide removed, and the filtrate evaporated gave 49.2 g. 2-bromo-N-methyl2-phenylsuccinimide (IV), m. 110.5-12°. IV (7.5 g.) in 75 ml. C6H6 and 3 g. NEt3 kept 1 hr. at room temperature and the product separated gave 3.7 g. N-methyl-2-phenylmaleimide (V), m. 147-8°. Arylation of maleimide with 3,4,5-trimethoxyphenyldiazonium chloride gave 27% 2-chloro-3-(3,4,5-trimethoxyphenyl)succinimide (VI), m. 207-8° (decomposition). VI (2 g.) heated 0.5 hr. with 8 ml. 2,6-lutidine gave 1.5 g. 2-(3,4,5-trimethoxyphenyl)maleimide (VII), m. 211-13°. VII (2.8 g.) in 75 ml. THF brought to reflux with 0.24 g. NaH, then treated in 45 min. under reflux with 7 g. MeI in 10 ml. THF, the mixture refluxed 1.75 hrs., evaporated, and the residue taken up in CHCl8 gave 2 g. N-methyl-2-(3,4,5-trimethoxyphenyl)maleimide, m. 155-66deg;. V (8.9 g.) in 150 ml. CH2Cl2 treated in one lot with 0.054 mole MeCHN2 in Et2O gave 11.6 g. N,5-dimethyl-3-phenyl-1-pyrazoline-3,4-dicarboximide (VIII), m. 106-76deg; (decomposition). VIII (5.1 g.) in 50 ml. alc. was heated 0.5 hr., evapd, in vacuo, and the 4.4 g. of oil subjected to partition chromatography. Evaporation of material from the first peak gave 5% N-methyl-2-ethyl-3phenylmaleimide, m. 69-70°. The 2nd and slower moving component was obtained as the chief yield, 4 g., of N,3-dimethyl-1-phenyl-1,2-cyclopropanedicarboximide.
Journal of Organic Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Formula: C3H9ClOS.
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