Pyridine → P-Toluenesulfonamide

HRID 266400Notes

Reaction equation

HRID 266400 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-])(=[O:3])=[O:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N:23]1C=CC=CC=1>>[S:1]([NH2:23])([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:3])=[O:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 85570p-Toluenesulfonate

Product 1

HCID 6269P-ToluenesulfonamideYield 95%

Procedure

The tosylate salt 3 (1.0 g; 0.0022 mol) was dissolved in pyridine (5.0 ml). p-Toluenesulfonyl chloride (476 mg; 0.0025 mol) was added and the reaction mixture stirred for 2 hours and concentrated. The residue was partitioned between THF/brine. The organic layer was washed with dilute HCl then with dilute K2CO3, and dried over MgSO4, and concentrated. The residue was placed on 50 g of silica and eluted with 50 mL of 50% EtOAc/heptane. The solution was concentrated to an oil which slowly crystallized to yield 913 mg (95%) of compound 4.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between THF/brine
  3. washThe organic layer was washed with dilute HCl
  4. dry with materialwith dilute K2CO3, and dried over MgSO4
  5. concentrationconcentrated
  6. washeluted with 50 mL of 50% EtOAc/heptane
  7. concentrationThe solution was concentrated to an oil which
  8. customslowly crystallized

Sources & evidence

ORD record
ord-08f6833c41014328bb0e76d0f05e7f82
Source dataset
uspto-grants-1997_07
Patent number
US05650535

Reaction notes

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