Anthranilic Acid → 1,3-Dithiaindane, 2-(3-methylbutyl)oxy-

HRID 483959

반응식

HRID 483959 반응식
[CH2:1]([OH:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[C:7](=[S:9])=[S:8].C(O)(=O)[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)N>ClCCCl.O1CCOCC1>[CH2:1]([O:6][CH:7]1[S:9][C:17]2[CH:16]=[CH:15][CH:14]=[CH:12][C:11]=2[S:8]1)[CH2:2][CH:3]([CH3:5])[CH3:4]

참가 물질

6

반응물 3

HCID 227Anthranilic AcidHCID 6348Carbon DisulfideHCID 31260Isoamyl Alcohol

생성물 1

HCID 5926411,3-Dithiaindane, 2-(3-methylbutyl)oxy-수율 40%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

42.1 g (0.36 mole) of isoamyl nitrile, 52.8 g (0.60 mole) of isoamyl alcohol and 150 ml of carbon disulfide were dissolved in 800 ml of 1,2-dichloroethane. The reaction solution was mildly heated under reflux at a temperature of about 80° C. A solution of 41.1 g (0.30 mole) of anthranilic acid in 100 ml of dioxane was added dropwise to the reaction solution over 1.5 hours. The reaction solution was further heated under reflux for an additional 30 minutes. The resulting mixture was washed successively with water, a saturated aqueous solution of sodium carbonate and water, and then dried over magnesium sulfate. The resulting organic solution was concentrated under reduced pressure. The residue was then purified through silica gel column chromatography (75 to 230 mesh; eluent: benzene) to obtain 28.8 g (yield: 40%) of the desired compound (V) as a pale yellow oil. The physical properties of the compound were as follows:

후처리

  1. temperatureThe reaction solution was mildly heated
  2. temperatureThe reaction solution was further heated
  3. temperatureunder reflux for an additional 30 minutes
  4. washThe resulting mixture was washed successively with water
  5. dry with materiala saturated aqueous solution of sodium carbonate and water, and then dried over magnesium sulfate
  6. concentrationThe resulting organic solution was concentrated under reduced pressure
  7. customThe residue was then purified through silica gel column chromatography (75 to 230 mesh; eluent: benzene)

출처 및 근거

ORD 기록
ord-b04ebeed25cb4373ae090a505820565d
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05229238

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