1,3-Propanedithiol → [4-(3-Mercaptopropylsulfanyl)-3-methylpyridin-2-yl]methanol

HRID 1637614노트

반응식

HRID 1637614 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([SH:11])[CH2:8][CH2:9][SH:10].Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][OH:21])[C:15]=1[CH3:22]>O>[SH:10][CH2:9][CH2:8][CH2:7][S:11][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][OH:21])[C:15]=1[CH3:22]

참가 물질

5

반응물 3

HCID 80131,3-PropanedithiolHCID 11430Potassium CarbonateHCID 16095907(4-Chloro-3-methyl-2-pyridinyl)methanol hydrochloride

생성물 1

HCID 18404145[4-(3-Mercaptopropylsulfanyl)-3-methylpyridin-2-yl]methanol수율 69.3%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
80 °C

실험 절차

A solution of potassium carbonate (691 g, 5 mol) in 1.5 l of water is treated with 1,3-propanedithiol (432.8 g, 4 mol) under a nitrogen atmosphere and heated to 80° C. A solution of (4-chloro-3-methylpyridin-2-yl)methanol hydrochloride (194.1 g, 1 mol) in 400 ml of water is then added dropwise at this temperature with vigorous stirring during the course of about 2 h. The mixture is additionally stirred at 80 to 85° C. for 18 h and then cooled to room temperature. After separating off the aqueous phase, the organic phase is treated with toluene (1.5 l) and washed with water (2×1 l). The organic phase is then extracted with 2M hydrochloric acid (2 l). The hydrochloric acid phase is concentrated and the residue is recrystallized from isopropanol. 159 g (60%) of the title compound are isolated. The crude product is employed without further purification for the synthesis of the compound of Example 1.

후처리

  1. stirringThe mixture is additionally stirred at 80 to 85° C. for 18 h
  2. temperaturecooled to room temperature
  3. customAfter separating off the aqueous phase
  4. additionthe organic phase is treated with toluene (1.5 l)
  5. washwashed with water (2×1 l)
  6. extractionThe organic phase is then extracted with 2M hydrochloric acid (2 l)
  7. concentrationThe hydrochloric acid phase is concentrated
  8. customthe residue is recrystallized from isopropanol

출처 및 근거

ORD 기록
ord-ec4eb38a64b045939f884a1987e9437b
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06043242

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