m-Chloroperbenzoic acid → 2-[(4-Chlorobenzene-1-sulfinyl)methyl]pyridine

HRID 1074924Notes

Reaction equation

HRID 1074924 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:22]>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:22])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 129532882-{[(4-Chlorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

Product 1

HCID 127602272-[(4-Chlorobenzene-1-sulfinyl)methyl]pyridineYield 37.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 2-(((4-chlorophenyl)thio methyl) pyridine, hydrochloride (2.0 g) in methylene chloride (50 ml) at 0° C. was treated with a solution of m-chloroperoxybenzoic acid (1.7 g) in CH2Cl2 (25 ml). The mixture was allowed to warm to ambient temperature and was stirred for 5 hours. The solution was washed with saturated sodium carbonate solution and water, then dried (MgSO4). The residue was dissolved in acetone and converted into the hydrochloride with ethereal HCl. N.m.r. showed approximately 20% of starting material remaining so the material was suspended in methylene chloride (50 ml) and treated with further m-chloroperoxybenzoic acid (2×500 g). The solution was washed with saturated sodium carbonate solution and water, dried (MgSO4) evaporated and the residue was dissolved in acetone and the hydrochloride precipitated with ethereal HCl solution. Recrystallisation from acetone-ether gave the title compound as the hydrochloride (0.7 g) mp 170° C. decomp. (Found: C,49.2; H,3.8; N,4.5 C12H10ClNOS.HCl.1/4 H2O requires C,49.2; H,4.0; N,4.8%).

Workup

  1. washThe solution was washed with saturated sodium carbonate solution and water
  2. dry with materialdried (MgSO4)
  3. dissolutionThe residue was dissolved in acetone
  4. additiontreated with further m-chloroperoxybenzoic acid (2×500 g)
  5. washThe solution was washed with saturated sodium carbonate solution and water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. dissolutionthe residue was dissolved in acetone
  9. customthe hydrochloride precipitated with ethereal HCl solution
  10. customRecrystallisation from acetone-ether

Sources & evidence

ORD record
ord-98587f217ed548ac94c0b26d998b6dae
Source dataset
uspto-grants-1983_07
Patent number
US04394509

Reaction notes

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