4-Toluenesulfonyl chloride → HCID 21998977, compound

HRID 1976609Notes

Reaction equation

HRID 1976609 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH:2]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C([N:25](C(C)C)CC)(C)C>C(Cl)Cl>[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([O-:10])(=[O:19])=[O:18])=[CH:13][CH:12]=1.[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][NH3+:25])[CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 178613-PyridinepropanolHCID 81531Diisopropylethylamine

Product 1

HCID 21998977HCID 21998977, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-(3-pyridyl)propanol (3.5 mL, 27.12 mmoles) in methylene chloride (15 mL) at 0° C. was treated with p-toluenesulfonyl chloride (6.7219 g, 1.3 equiv.) and diisopropylethylamine (6.14 mL, 1.3 equiv.). After 10 minutes, the mixture was warmed to room temperature. After a further 4 hours, the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate and evaporated. the residue was chromatographed on silica, eluting with ethyl acetate, to give a thick, pale-yellow oil which was immediately dissolved in saturated ammonialmethanol (165 mL). This was left to stand at room temperature for 5 days at which time the solvent was removed under reduced pressure. The residue was dried under high vacuum and then dissolved as far as possible in ether (150 mL). The resulting solid product was collected by filtration, washed with ether, and dried in vacuo (6.3051 g, 76%).

Workup

  1. waitAfter a further 4 hours
  2. customthe solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customthe residue was chromatographed on silica
  8. washeluting with ethyl acetate
  9. customto give a thick, pale-yellow oil which
  10. dissolutionwas immediately dissolved in saturated ammonialmethanol (165 mL)
  11. waitThis was left
  12. waitto stand at room temperature for 5 days at which time
  13. customthe solvent was removed under reduced pressure
  14. customThe residue was dried under high vacuum
  15. dissolutiondissolved as far as possible in ether (150 mL)
  16. filtrationThe resulting solid product was collected by filtration
  17. washwashed with ether
  18. customdried in vacuo (6.3051 g, 76%)

Sources & evidence

ORD record
ord-b924edbdd9dc4e7eb2bbea888a81ff17
Source dataset
uspto-grants-2001_05
Patent number
US06228872B1

Reaction notes

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