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

HRID 523449

반응식

HRID 523449 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-98fa62764e0f4df29978c5879b2d56e5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09337430B2

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