Dichloromethane → HCID 10857214, compound

Temperature

20 °C

To 62.9 parts of (S)-1,2-propanediamine under a nitrogen atmosphere (temp. 0°-5° C.) was added dropwise over 7 hours a solution of 80.84 parts of 4-methylbenzenesulfonyl chloride in 1689 parts of dichloromethane. After stirring overnight at 20° C., the reaction mixture was washed with 250 parts of water (3×). The organic layer was separated, dried, filtered and evaporated. About 1 gram of the thus obtained product was recrystallized from 2-propanol. After cooling to 0° C,, filtering and drying, about 0.30 parts of crystals suitable for seeding were obtained. The remainder of the product was dissolved in 4-methyl-2-pentanol by heating just below the reflux temperature. The mixture was allowed to cool slowly and at about 30° C. was seeded with the previously obtained crystals. After further cooling to 0° C., the precipitate was filtered off and triturated with 2,2'-oxybispropane. The crystals were filtered off, dried in vacuo, yielding 50.75 parts (52.4%) of (S)-N-2-aminopropyl-4-methylbenzenesulfonamide; mp. 82°-86° C.; [α]20D =-1.10° (c =1% in methanol) (interm. 1).

1. washthe reaction mixture was washed with 250 parts of water (3×)
2. customThe organic layer was separated
3. customdried
4. filtrationfiltered
5. customevaporated
6. customAbout 1 gram of the thus obtained product was recrystallized from 2-propanol
7. temperatureAfter cooling to 0° C
8. filtrationfiltering
9. customdrying, about 0.30 parts of crystals suitable for seeding
10. customwere obtained
11. temperatureby heating just below the reflux temperature
12. temperatureto cool slowly and at about 30° C.
13. temperatureAfter further cooling to 0° C.
14. filtrationthe precipitate was filtered off
15. customtriturated with 2,2'-oxybispropane
16. filtrationThe crystals were filtered off
17. customdried in vacuo

ORD record

ord-c6b6af4a917e4d24906380f964308205

Source dataset

uspto-grants-1996_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05543570