Sodium Sulfite → Sodium 7-(3,4,5-triphenyl-2-oxo-2,3-dihydroimidazol-1-yl)heptanesulphonate

HRID 1742275노트

반응식

HRID 1742275 반응식
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)[C:8]2=[O:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:33]([O-:36])([O-:35])=[O:34].[Na+:37].[Na+]>C(O)C.O>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:33]([O-:36])(=[O:35])=[O:34])[C:8]2=[O:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+:37]

참가 물질

5

반응물 2

HCID 24437Sodium Sulfite2회HCID 229163881,4,5-Triphenyl-3-(7-bromoheptyl)imidazol-2-one

생성물 1

HCID 23671144Sodium 7-(3,4,5-triphenyl-2-oxo-2,3-dihydroimidazol-1-yl)heptanesulphonate수율 23.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

A solution of 1,4,5-triphenyl-3-(7-bromoheptyl)-imidazol-2-one (2.0 g) in ethanol (10 ml) was refluxed with a solution of sodium sulphite (0.55 g) in water (5 ml) for 20 hours. More sodium sulphite (0.2 g) was added and refluxing continued for a further 20 hours. The mixture was evaporated to dryness, boiled in ethanol, filtered hot and evaporated to an oil. This was taken up in a small volume of ethanol, excess diethyl ether added and the precipitated solid filtered off and chromatographed on silica gel (dichloromethane/methanol 5:1). The resulting oil in methanol/water 1:1 was passed down an Amberlyst 15 ion exchange resin (Na form) and evaporated to a solid. This was taken up in ethanol and precipitated with diethyl ether giving sodium 7-(3,4,5-triphenyl-2-oxo-2,3-dihydroimidazol-1-yl)heptanesulphonate (0.49 g), 23%) as a white solid, m.p. 160° C.

후처리

  1. temperaturerefluxing
  2. customThe mixture was evaporated to dryness
  3. filtrationfiltered hot
  4. customevaporated to an oil
  5. additionadded
  6. filtrationthe precipitated solid filtered off
  7. customchromatographed on silica gel (dichloromethane/methanol 5:1)
  8. customevaporated to a solid
  9. customprecipitated with diethyl ether

출처 및 근거

ORD 기록
ord-7608b3cc5c944635b7cd0d567d7bea6e
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05338752

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