4-Toluenesulfonyl chloride → HCID 24995121, compound

HRID 655993Notes

Reaction equation

HRID 655993 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][N:11]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1050975-Phenyl-2-pyridinamine

Product 1

HCID 24995121HCID 24995121, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-phenylpyridin-2-amine (340 mg, 2 mmol) in dry pyridine (10 mL) was added 4-methylbenzenesulfonyl chloride (427 mg, 2.24 mmol). The solution was stirred at room temperature under Argon. The pyridine was then removed in vacuo and flashed off with toluene. The residue was partitioned between EtOAc and 1M NaOH. The organic phase was washed with 1M NaOH until no turbidity was observed on rectification of a small sample. The alkaline phase was made acidic (˜pH 3) with 1M HCl and extracted with EtOAc. After drying over Na2SO4, solvent was removed in vacuo. The crude product weighed 0.24 g. The crude product was taken up in 10 mL of hot EtOAc, diluted with 10 mL of hexane and seeded to give 209 mg of white needles with mp 187-189° C.

Workup

  1. customThe pyridine was then removed in vacuo
  2. customThe residue was partitioned between EtOAc and 1M NaOH
  3. washThe organic phase was washed with 1M NaOH until no turbidity
  4. extractionextracted with EtOAc
  5. dry with materialAfter drying over Na2SO4, solvent
  6. customwas removed in vacuo
  7. additiondiluted with 10 mL of hexane

Sources & evidence

ORD record
ord-ab74b8b1903548069d00b9fbdfc1e2b2
Source dataset
uspto-grants-2011_12
Patent number
US08071631B2

Reaction notes

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