Potassium Hydroxide → HCID 13935142, 화합물

HRID 580719노트

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HRID 580719 반응식
[OH-].[K+].[NH2:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:19][C:20]([F:29])([F:30])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][NH:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

생성물 1

HCID 13935142HCID 13935142, 화합물수율 42%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매2회

실험 절차

In 150 ml of toluene and 700 ml of 30% potassium hydroxide were combined 3.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 0.72 g of tetrabutylammonium hydrogen sulfate. The reaction was mechanically stirred and heated with a steam bath. To it was added dropwise a solution of 13.5 g 3-trifluoromethylbenzyl bromide in 30 ml of toluene over 1 hour. After the addition, heating was continued 1 hour during which the reaction went to completion. The organic phase was separated, washed with ice-cold saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. The oil was diluted with 10 ml of ethyl acetate and purified by preparative HPLC (ethyl acetate). The product-containing fractions were evaporated and recrystallized from DCM/hexane to yield 2.20 g of solid, mp 147°-149° C.

후처리

  1. temperatureheated with a steam bath
  2. additionAfter the addition
  3. temperatureheating
  4. customThe organic phase was separated
  5. washwashed with ice-cold saturated NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to an oil
  9. additionThe oil was diluted with 10 ml of ethyl acetate
  10. custompurified by preparative HPLC (ethyl acetate)
  11. customThe product-containing fractions were evaporated
  12. customrecrystallized from DCM/hexane

출처 및 근거

ORD 기록
ord-13702dbeaeb74a738c780bc48513ead8
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04754050

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