9,9-Dimethyl-9,10-dihydroacridine → 10-(2-Bromobenzyl)-9,9-dimethyl-9,10-dihydroacridine

HRID 523449

反応式

HRID 523449 の反応式
[H-].[Na+].[CH3:3][C:4]1([CH3:18])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.[Br:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br>CN(C)C=O>[Br:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][N:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:18])([CH3:3])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2

参加物

5

反応物 3

HCID 226479,9-Dimethyl-9,10-dihydroacridineHCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromide

生成物 1

HCID 8673266410-(2-Bromobenzyl)-9,9-dimethyl-9,10-dihydroacridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

9.7 g (0.243 mol) of NaH, 60% in mineral oil, are dissolved in 500 ml of dimethylformamide under protective atmosphere. 22.1 g (0.106 mol) of 9,9-dimethyl-9,10-dihydroacridine are dissolved in 500 ml of DMF and added dropwise to the reaction mixture. After 1 h at room temperature, a solution of 60.6 (242 mmol) of 2-bromobenzyl bromide in 500 ml of DMF is added dropwise. The reaction mixture is stirred at room temperature for 1 h, then poured onto ice and extracted three times with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is extracted with hot toluene and recrystallised from toluene/n-heptane. The yield is 37 g (94%).

後処理

  1. additionadded dropwise to the reaction mixture
  2. additionpoured onto ice
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. extractionThe residue is extracted with hot toluene
  7. customrecrystallised from toluene/n-heptane

出典と根拠

ORDレコード
ord-98fa62764e0f4df29978c5879b2d56e5
出典データセット
uspto-grants-2016_05
特許番号
US09337430B2

関連ノート

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