Hydroxide → HCID 13935142、化合物

HRID 1904717ノート

反応式

HRID 1904717 の反応式
[OH-].[NH2:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[C:15](=[O:17])[CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:18][C:19]([F:28])([F:29])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH:2][C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[C:15](=[O:17])[CH2:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2

参加物

6

反応物 3

HCID 961HydroxideHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

生成物 1

HCID 13935142HCID 13935142、化合物収率 42%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 1140Toluene溶媒2 回

実験手順

In 150 ml of toluene and 700 of 30% potassisum 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.

後処理

  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

出典と根拠

ORDレコード
ord-81d1aa38fe8e4fa2a77e073f89f6eed7
出典データセット
uspto-grants-1989_06
特許番号
US04839364

反応ノート

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