Kochetkov, N. K. published the artcileCycloserine and related compounds. VIII. Synthesis of 3-isoxazolidones, Category: chlorides-buliding-blocks, the publication is Zhurnal Obshchei Khimii (1959), 3417-24, database is CAplus.
cf. CA 54, 8777i. Halo hydroxamic acids were prepared by a general reaction of acyl chlorides with H2NOH in aqueous medium, the products being cyclized to 3-isoxazolidones by MeOH-KOH. To 32 g. NaOH in 120 ml. H2O was added at 0° 55.5 g. NH2OH.HCl and the resulting solution was treated below 5° with 68.6 g. BrCH2CH2COCl. After 1 hr. at 0-5°, 1.5 hrs. at 15°, the mixture was heated to 60° and filtered. The filtrate after 1-2 days at -5° gave 48-50% BrCH2CH2CONHOH (I), m. 88-90°. Similarly were prepared: 50-5% ClCH2CH2CONHOH, m. 102-4°; 52-5% BrCH2CHMeCONHOH, m. 98-100°; 61% PhCHBrCH2CONHOH, m. 85-90°; 65% ClCMe2CH2CONHOH, an oil; PhCH:CPhCONHOH (from PhCHBrCHPhCOCl), 50%, m. 147-9°; BrCH2CHBrCONHOH, 55-60%, m. 151-3°: 50-60% ClCH2CHClCONHOH, m. 95-7°. I (6.8 g.) in 15 ml. MeOH was treated with 40 ml. 2N MeOH-KOH and heated 40 min., yielding after filtration and evaporation and treatment of the residue with Et2O 80-5% K salt of 3-isoxazolidone, decomposed 213-15°, which with aqueous AgNO3 gave the Ag salt, decomposed 166-8°. The K salt treated with absolute EtOH-HCl gave 70% 3-isoxazolidone, m. 69-70°. Similarly, were prepared: 70% K salt of 4-methyl-3-isoxazolidone, decomposed 151-3° (free base decomposed 72-4°); 70% K salt of 5-phenyl-3-isoxazolidone, decomposed 285-7° (free base m. 121-3°); 50% K salt of 5,5-dimethyl-3-isoxazolidone, m. 122-5° (Ag salt, decomposed 166-8°; free base, an unpurifiable oil). The K salt of 3-isoxazolidone and BzCl in dioxane gave 47% N-benzoyl-3-isoxazolidone, m. 123-4°, also formed from the Ag salt in 40% yield. Similarly were prepared: 51% N-(p-nitrobenzoyl)-3 isoxazolidone, m. 178-80°, and 40% N-carbomethoxy-3-isoxazolidone, m. 106-8°.
Zhurnal Obshchei Khimii published new progress about 18791-02-1. 18791-02-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 2,3-Dibromopropionylchloride, and the molecular formula is C3H3Br2ClO, Category: chlorides-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics