1,3-Dithiolane-2-thione → 2,2'-[Thiobis(methylene)]bis-1,4,6,9-tetrathiaspiro[4.4]nonane

HRID 15244

반응식

HRID 15244 반응식
[C:1]1(=[S:6])[S:5][CH2:4][CH2:3][S:2]1.F[B-](F)(F)F.[H+].[S:13]([CH2:18][CH:19]1[CH2:21][S:20]1)[CH2:14][CH:15]1[CH2:17][S:16]1>ClCCl>[S:13]([CH2:14][CH:15]1[CH2:17][S:16][C:1]2([S:5][CH2:4][CH2:3][S:2]2)[S:6]1)[CH2:18][CH:19]1[CH2:21][S:20][C:1]2([S:5][CH2:4][CH2:3][S:2]2)[S:6]1

참가 물질

5

반응물 3

HCID 131961,3-Dithiolane-2-thioneHCID 28118Tetrafluoroboric acidHCID 109760661,1'-Thiobis(2,3-epithiopropane)

생성물 1

HCID 593415152,2'-[Thiobis(methylene)]bis-1,4,6,9-tetrathiaspiro[4.4]nonane수율 4.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-5 °C

실험 절차

A mixture of ethylene trithiocarbonate (5.04 g, 0.037 moles) and tetrafluoroboric acid (1.0 ml) in anhydrous dichloromethane (50.0 ml) cooled to −5° C. and stirred under nitrogen, was treated dropwise with a solution of 2,2′-[thiobis(methylene)]bis-thiirane (3.34 g, 0.019 moles) in anhydrous dichloromethane (30.0 ml). The resulting mire was allowed to warm to room temperature and quenched with 5% sodium bicarbonate solution (50.0 ml). The separation of the organic layer followed by water washing, drying and evaporation afford a wet yellow solid. Purification of which by short-path chromatography (20% ethyl acetate/hexane over silica) afforded 2,2′-[thiobis(methylene)]bis-1,4,6,9-tetrathiaspiro[4.4]nonane (4.7% yield).

후처리

  1. temperatureto warm to room temperature
  2. customquenched with 5% sodium bicarbonate solution (50.0 ml)
  3. customThe separation of the organic layer
  4. customdrying
  5. customevaporation
  6. customafford a wet yellow solid
  7. customPurification of which by short-path chromatography (20% ethyl acetate/hexane over silica)

출처 및 근거

ORD 기록
ord-d26563509c44439d949701404d266712
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732507B2

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