Sodium hydride → HCID 66797648, compound

HRID 2275953Notes

Reaction equation

HRID 2275953 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2=[CH:11][C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=[C:9]2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4.[H-].[Na+].Cl[C:26]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:29]=[C:28]([N:38]2[C:50]3[CH:49]=[CH:48][C:47]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[CH:46][C:45]=3[C:44]3[C:39]2=[CH:40][CH:41]=[C:42]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH:43]=3)[N:27]=1>CN(C)C=O>[C:57]1([C:42]2[CH:41]=[CH:40][C:39]3[N:38]([C:28]4[N:29]=[C:30]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:31]=[C:26]([N:13]5[C:12]6[CH:11]=[C:10]7[C:2]([CH3:22])([CH3:1])[C:3]8[C:8]([C:9]7=[CH:21][C:20]=6[C:19]6[C:14]5=[CH:15][CH:16]=[CH:17][CH:18]=6)=[CH:7][CH:6]=[CH:5][CH:4]=8)[N:27]=4)[C:50]4[C:45]([C:44]=3[CH:43]=2)=[CH:46][C:47]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[CH:48][CH:49]=4)[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 665852047,7-Dimethyl-5,7-dihydroindeno[2,1-b]carbazoleHCID 86663413HCID 86663413, compound

Product 1

HCID 66797648HCID 66797648, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

18.7 g (66.3 mmol) of 12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]-fluorene are dissolved in 200 ml of dimethylformamide under a protective-gas atmosphere, and 5.3 g of 60% NaH in mineral oil (73 mmol) are added. After 1 h at room temperature, a solution of 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-3,6-diphenyl-9H-carbazole (40.5 g, 79.5 mmol) in 150 ml of dimethylformamide is added dropwise. The reaction mixture is stirred at room temperature for 12 h. After this time, the reaction mixture is 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, recrystallised from dichloromethane/isopropanol and finally sublimed in a high vacuum, the purity is 99.9%. The yield is 21.4 g (28 mmol, 42%).

Workup

  1. additionare added
  2. additionAfter this time, the reaction mixture is poured 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 dichloromethane/isopropanol

Sources & evidence

ORD record
ord-11b6d32a48894d09ad9f9cac8cddb61c
Source dataset
uspto-grants-2015_09
Patent number
US09126970B2

Reaction notes

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