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1,2-Diaminocyclohexane, trans- → 9-(dibenzo[b,d]thiophen-4-yl)-3-fluoro-9H-carbazole

HRID 879914
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HRID 879914 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.I[C:16]1[C:21]2[S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:20]=2[CH:19]=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>[Cu]I.O1CCOCC1>[CH:19]1[C:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[S:22][C:21]=2[C:16]([N:6]2[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[CH:17][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 4583534-IododibenzothiopheneHCID 158868413-Fluorocarbazole

생성물 1

HCID 867225089-(dibenzo[b,d]thiophen-4-yl)-3-fluoro-9H-carbazole수율 48.1%

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 312751,4-Dioxane용매

실험 절차

A mixture of 6.7 g (36.2 mmole) 3-fluoro-9H-carbazole, 11.2 g (36.2 mmole) of 4-iododibenzo[b,d]thiophene, 17.1 g (90 mmole) of copper(I) iodide, 19.1 g (90 mmole) of potassium phosphate, 10.3 g (90 mmole) of trans-1,2-cyclohexanediamine and 1,4-dioxane 700 ml were refluxed under nitrogen for about overnight. Then, the solution was filtered at 110° C. To receive the filtrate, And the 1,4-dioxane was removed under reduced pressure from the filtrate. The filtrate was extracted with 500 ml dichloromethane and 2000 ml water, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-ethyl acetate) to give product 6.4 g (48%).

후처리

  1. temperaturewere refluxed under nitrogen for about overnight
  2. filtrationThen, the solution was filtered at 110° C
  3. customthe 1,4-dioxane was removed under reduced pressure from the filtrate
  4. extractionThe filtrate was extracted with 500 ml dichloromethane and 2000 ml water
  5. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified by column chromatography on silica (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-c71573ea9d664314be50bf5f1de4d2dd
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08993130B2

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