m-Chloroperbenzoic acid → Hydrochloric Acid

HRID 2286222ノート

反応式

HRID 2286222 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:6]=[CH:7][C:8]=1[Cl:9].[Cl:18]C1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[C:5]([S:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:23])[CH:6]=[CH:7][C:8]=1[Cl:9].[ClH:18]

参加物

5

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 127602202-{[(3,4-Dichlorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

生成物 2

HCID 313Hydrochloric Acid収率 252.3%HCID 127602292-[(3,4-Dichlorobenzene-1-sulfinyl)methyl]pyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A suspension of 2-(((3,4-dichlorophenyl)thio)methyl)pyridine, hydrochloride (2.0 g) in methylene chloride (50 ml) at 0° C. was treated with a solution of m-chloroperoxybenzoic acid (1.5 g) in methylene chloride (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 35% 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 propan-2-ol/ether gave the title compound, hydrochloride (0.6 g) mp 178° C. decomp (Found: C44.7; H,3.2; N,4.2. C12H9Cl2NOS.HCl requires C,44.7; H,3.1; N,4.3%).

後処理

  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 propan-2-ol/ether

出典と根拠

ORDレコード
ord-09606a99d93b466aa01d93840a22f160
出典データセット
uspto-grants-1982_04
特許番号
US04327102

反応ノート

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