m-Chloroperbenzoic acid → 2H-Pyrano(2,3-b)pyridine, 2-(3,4-dichlorophenyl)-3,4-dihydro-6-(methylsulfinyl)-

HRID 280200노트

반응식

HRID 280200 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:20][C:13]3=[N:14][CH:15]=[C:16]([S:18][CH3:19])[CH:17]=[C:12]3[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:20][C:13]3=[N:14][CH:15]=[C:16]([S:18]([CH3:19])=[O:26])[CH:17]=[C:12]3[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 5149062-(3,4-Dichlorophenyl)-3,4-dihydro-6-(methylthio)-2h-pyrano[2,3-b]pyridine

생성물 1

HCID 5149022H-Pyrano(2,3-b)pyridine, 2-(3,4-dichlorophenyl)-3,4-dihydro-6-(methylsulfinyl)-

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-5 °C

실험 절차

To a stirred solution of 1.0 g of 2-(3,4-dichlorophenyl)-3,4-dihydro-6-(methylthio)-2H-pyrano[2,3-b]pyridine in 25 ml of methylene chloride at -25° C. there was added dropwise a solution of 0.55 g of 80-85% m-chloroperoxybenzoic acid in 20 ml of methylene chloride over 5-10 minutes while keeping the temperature between -20° and -30° C. A precipitate formed. The mixture was then allowed to warm to -5° C. over 2 hours and then extracted with aqueous saturated sodium bicarbonate solution, aqueous saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure to leave a pale yellow solid. This was recrystallized from a mixture of ethyl acetate and hexane to give 2-(3,4-dichlorophenyl)-3,4-dihydro-6-(methylsulfinyl)-2H-pyrano[2,3-b]pyridine as a cream-colored solid melting at about 159°-162° C.

후처리

  1. customthe temperature between -20° and -30° C
  2. customA precipitate formed
  3. extractionextracted with aqueous saturated sodium bicarbonate solution, aqueous saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto leave a pale yellow solid
  7. customThis was recrystallized from a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-82478400a44a4653986ff8d0fe8f1ed6
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588733

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