m-Chloroperbenzoic acid → Hydrochloric Acid

HRID 1074926노트

반응식

HRID 1074926 반응식
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]

참가 물질

5

반응물 2

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

생성물 2

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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 with 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%).

후처리

  1. washThe solution with 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

출처 및 근거

ORD 기록
ord-9ce6cfce0cc64e6fb99a7fbc1903c40b
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04394509

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