4-Toluenesulfonyl chloride → HCID 10857214, compound

HRID 1449833Notes

Reaction equation

HRID 1449833 reaction equation
[CH2:1]([NH2:5])[C@@H:2]([NH2:4])[CH3:3].[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>ClCCl>[NH2:4][C@@H:2]([CH3:3])[CH2:1][NH:5][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:6])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 642322(2S)-propane-1,2-diamine

Product 1

HCID 10857214HCID 10857214, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

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 (3x). The organic layer was separated dried, filtered and evaporated. About 1 gram of the thus obtained 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]D20 =-1.10° (c=1% in methanol) (interm.1).

Workup

  1. washthe reaction mixture was washed with 250 parts of water (3x)
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionAbout 1 gram of the thus obtained product was dissolved in 4-methyl-2-pentanol
  7. temperatureby heating just below the reflux temperature
  8. temperatureto cool slowly and at about 30° C.
  9. temperatureAfter further cooling to 0° C.
  10. filtrationthe precipitate was filtered off
  11. customtriturated with 2,2'-oxybispropane
  12. filtrationThe crystals were filtered off
  13. customdried in vacuo

Sources & evidence

ORD record
ord-171078ba5f894cfa823ac7a1466b1412
Source dataset
uspto-grants-1997_02
Patent number
US05599982

Reaction notes

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