Helberger, Johann H. published the artcileOrganic sulfonic acids. VII. Preparation and reactions of 3-halo-1-propanesulfonamides, Synthetic Route of 55788-44-8, the publication is Justus Liebigs Annalen der Chemie (1963), 67-74, database is CAplus.
cf. CA 49, 9486c. KBr (47.6 g.) in 70 cc. H2O treated with 48.8 g. molten 1,3-propanesultone (I) at 60° with stirring, stirred several min. until I dissolved, evaporated on a H2O bath, and the residue cooled, washed with cold EtOH, and dried in vacuo gave (in 2 crops) 76.7 g. X(CH2)3SO3R (II) (X = Br, R = K) (III), which was recrystallized from 3:1 EtOH-H2O for analysis. Molten I (35 g.) added to 42 g. NaBr in 38 cc. H2O with continuous stirring and worked up gave (in 2 crops) 54 g. II (X = Br, R = Na) (IIIa). NaCl (4 g.) in 15 cc. H2O treated in 1 lot with 8.2 g. molten I at 60° with stirring, stirred until complete solution, and evaporated (H2O bath) gave (in 2 crops) 11.7 g. II (X = Cl, R = Na) (IV). III (21.6 g.) mixed with 24 g. PCl5 in small portions with stirring, the resulting oil heated 10 min. at 70° (H2O bath), cooled, poured in small portions into ice H2O with stirring, stirred 1 hr. below 20°, extracted with Et2O, the extract washed with H2O and aqueous NaHCO3, added portionwise to 21 cc. 25% aqueous NH3, the aqueous phase extracted with 5 15-cc. portions Et2O, the combined Et2O solutions dried, and evaporated in vacuo gave 8.5 g. X(CH2)3SO2NRR’ (V) (X = Br, R = R’ = H) (VI), m. 59-61° (CHCl3). IV (9 g.) treated with 14 g. PCl5 like VI, the sulfonyl chloride extracted with Et2O, the extract washed with H2O, and aqueous NaHCO3, added portionwise to 15 cc. 25% aqueous NH3 at below 15° with stirring and ice cooling, stirred 20 min., and the product which separated washed with 5 cc. 1:2 Et2O-petr. ether gave (including product obtained from the mother liquors) 4 g. V (X = CIl R = R’ = H), m. 63-5°. Finely powd. dry II (X = iodine, R = Na) (VII) (prepared like IV) added portionwise to 34.5 g. PCl5 with stirring and cooling, the viscous mixture kept 6 hrs. at room temperature, heated 10 min. at 70°, cooled, poured into ice H2O with stirring keeping the temperature below 20°, the sulfonyl chloride containing some iodine extracted with Et2O, the extract decolorized with a little NaHSO8, washed with H2O and aqueous NaHCO3, added portionwise to 30 cc. 25% aqueous NH3 with stirring and ice cooling, and stirred 0.5 hr. at below 10° gave 19.6 g. V (X = iodine, R = R’ = H) (VII), m. 94-6° (H2O). VII (13.6 g.) treated similarly with 10.3 g. PCl5, the Et2O solution of the sulfonyl chloride treated at 5° with 25 cc. Me2NH with stirring keeping the temperature below 10° until the product crystallized, the precipitate washed twice with 5 cc. ice H2O, and recrystd, from EtOH with C gave 5.7 g. V (X = iodine, R = R’ = Me), m. 67-8° (EtOH). IV (9 g.) treated with 14 g. PCl5 like VI, the Et2O solution of the sulfonyl chloride treated with 10.5 g. p-MeC6H4NH2 (IX) in Et2O at 20°, kept several days, filtered, the filtrate washed with dilute HCl, dried, concentrated in vacuo, and recrystallized from EtOH-H2O gave 7 g. V (X = Cl, R = H, R’ = C6H4Me-p), m. 73-5° (EtOH-H2O). IIIa (20.3 g.) treated with 24 g. PCl5, the Et2O solution of the sulfonyl chloride added to 19.3 g. IX in 80 cc. Et2O at room temperature, kept several days, filtered, the filtrate washed with dilute HCl, dried, concentrated in vacuo and the residue recrystallized from 2:1 EtOH-H2O (solvent A) gave 13.2 g. V (X = Br, R = H, R’ = C6H4Me-p)(X),m. 66-7°(A). X(2.5 g.)and 10 g. Ac2O refluxed 3 hrs., cooled, poured into ice H2O, and kept 3 hrs. gave 2.5 g. N-Ac derivative (XI) of X, m. 87-8° (80% MeOH). VII (6.8 g.) treated with 6 g. PCl5 like VIII, the Et2O solution of the sulfonyl chloride combined with 6 g. IX in 25 cc. Et2O at 20°, kept several days, filtered, the filtrate washed repeatedly with dilute HCl, dried, concentrated in vacuo, and the residue crystallized from 14 cc. EtOH gave 4.5 g. V (X = iodine, R = H, R’ = C6H4Me-p), m. 69-70° (EtOH with C); 98% N-Ac derivative m. 75-8° (EtOH). III (21.6 g.) treated with 24 g. PCl5 like VI, the Et2O solution of the sulfonyl chloride added portionwise to 16.8 g. PhNH2 in 50 cc. Et2O at 20°, kept several days, filtered, the filtrate washed with dilute HCl, dried, concentrated in vacuo, and the residual oil repeatedly evaporated with EtOH gave 46% V (X = Br, R = H, R’ = Ph) (XII), m. 53-5° (A); 73% N-Ac derivative m. 103-5° (EtOH). III (21.6 g.) treated with 24 g. PCl5, the Et2O solution of the sulfonyl chloride added to 21.8 g. 2,6-Me2C6H3NH2 in 100 cc. Et2O at 20°, kept at room temperature, the filtrate extracted with 5% HCl, dried, evaporated in vacuo, and the residue recrystallized from 60% aqueous EtOH (solvent B) with C gave 8.7 g. V (X = Br, R = H, R’ = C6H3Me22-,6), m. 103-4° (B). III (21.6 g.) treated with 24 g. PCl5 like VI, the Et2O (20 cc.) solution of the sulfonyl chloride added to 16.8 g. PhNH2 in 50 cc. Et2O at 20°, kept 24 hrs. at room temperature, filtered, the filtrate extracted repeatedly with 5% HCl, dried, evaporated in vacuo, the residual sirup repeatedly evaporated with EtOH, and the solid recrystallized from 80% aqueous MeOH and then from EtOH with C gave 2.4 g. V (X = PhNH, R = H, R’ = Ph) HCl salt, m. 156-7° (aqueous-alc.-HCl). X (10.2 g.) in 40 cc. C6H6 combined with 5.1 g. Et2NH at room temperature, refluxed 3 hrs., cooled, filtered, the filtrate evaporated in vacuo, the residual sirup treated with 8 cc. EtOH, the precipitate (3.8 g.) filtered, washed with cold EtOH, and recrystallized from 16 cc. EtOH gave 3.5 g. 2-(p-tolyl)isothiazolidine 1,1-dioxide (XIII), m. 91-3°; the filtrate gave 2.8 g. V (X = Et2N, R = H, R’ = C6H4Me-p) HCl salt (XIV.HCl), m. 144-6° (EtOH). To 7.3 g. Et2NH was added portionwise 5.5 g. X (the temperature rose to 40°), kept 6 hrs. at room temperature, diluted with 30 cc. C6H6, filtered, the filtrate evaporated, and the residual solid recrystallized from EtOH to give 2.3 g. XIII. m. 90-3°; the mother liquor with 5% EtOH-HCl gave 1.3 g. XIV.HCl, m. 141-3° (EtOH). XII (4.2 g.) in 25 cc. C6H6 combined with 2.2 g. Et2NH at 20°, refluxed 3 hrs., cooled, filtered, and the filtrate concentrated deposited 1.8 g. 2-phenylisothiazolidine 1,1-dioxide, m. 119-21° (EtOH); the mother liquor treated with 10% EtOH-HCl evaporated, and the residual sirup which crystallized on prolonged standing recrystallized twice from 10% EtOH-HCl with C gave 1 g. V (X = Et2N, R = H, R’ = Ph) HCl salt, m. 147-9° (EtOH-HCl). XI (5 g.) in 25 cc. C6H6 refluxed 3 hrs. with 2.2 g. Et2NH, cooled, filtered, the filtrate evaporated, the sirupy residue seeded with XIII, and worked up like XIII gave 0.4 g. XIII, m. 88-91°; the mother liquor worked up like XIV.HCl gave 1.1 g. XIV.HCl, m. 142-5°.
Justus Liebigs Annalen der Chemie published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C3H6BrNaO3S, Synthetic Route of 55788-44-8.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary