HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dodecane → N,N'-bis[4-{bis(biphenyl-4-yl)amino}biphenyl-4'-yl]-N,N'-diphenyl-4,4''-diamino-p-terphenyl

HRID 602219
Notes
Print preview

Reaction equation

HRID 602219 reaction equation
[C:1]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:6]=[CH:5][C:4]([N:7]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.I[C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][C:55]([C:58]3[CH:63]=[CH:62][C:61](I)=[CH:60][CH:59]=3)=[CH:54][CH:53]=2)=[CH:48][CH:47]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82]>C1(C)C=CC=CC=1.[Cu].C(OCC)(=O)C>[C:30]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:32][C:27]([N:7]([C:4]2[CH:3]=[CH:2][C:1]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:6][CH:5]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:46]4[CH:51]=[CH:50][C:49]([C:52]5[CH:57]=[CH:56][C:55]([C:58]6[CH:63]=[CH:62][C:61]([N:20]([C:80]7[CH:81]=[CH:82][C:77]([C:76]8[CH:71]=[CH:72][C:73]([N:7]([C:8]9[CH:9]=[CH:10][C:11]([C:14]%10[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=%10)=[CH:12][CH:13]=9)[C:4]9[CH:5]=[CH:6][C:1]([C:39]%10[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=%10)=[CH:2][CH:3]=9)=[CH:74][CH:75]=8)=[CH:78][CH:79]=7)[C:21]7[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=7)=[CH:60][CH:59]=6)=[CH:54][CH:53]=5)=[CH:48][CH:47]=4)=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)=[CH:28][CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 35635834,4''-Diiodo-p-terphenylHCID 23140819N4,N4-di([1,1'-biphenyl]-4-yl)-N4'-phenyl-[1,1'-biphenyl]-4,4'-diamine

Product 1

HCID 59510919N,N'-bis[4-{bis(biphenyl-4-yl)amino}biphenyl-4'-yl]-N,N'-diphenyl-4,4''-diamino-p-terphenyl
Yield 65.9%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

There were mixed 12.68 g (0.022 mole) of N,N-bis(biphenyl-4-yl)-N′-phenyl-4,4′-diaminobiphenyl, 5.00 g (0.01 mole) of 4,4″-diiodo-p-terphenyl, 4.14 g (0.030 mole) of anhydrous potassium carbonate, 0.32 g (0.005 mole) of copper powder and 10 ml of n-dodecane, followed by reaction at 195 to 210° C. for 30 hours. The reaction product was extracted with 800 ml of toluene, and the insoluble matter was removed by filtration. Then, the filtrate was concentrated. After the concentration, 100 ml of methanol was added to perform crystallization, and suction filtration was performed to obtain crude crystals. The crude crystals were dissolved in 300 ml of toluene under reflux, and allowed to cool down to 45° C. Then, 300 ml of ethyl acetate was added dropwise to perform crystallization, thereby obtaining crystals. N,N′-bis[4-{bis(biphenyl-4-yl)amino}biphenyl-4′-yl]-N,N′-diphenyl-4,4″-diamino-p-terphenyl was obtained in an amount of 9.43 g. The yield was 65.9%, and the HPLC purity was 94.7%.

Workup

  1. customfollowed by reaction at 195 to 210° C. for 30 hours
  2. extractionThe reaction product was extracted with 800 ml of toluene
  3. customthe insoluble matter was removed by filtration
  4. concentrationThen, the filtrate was concentrated
  5. concentrationAfter the concentration, 100 ml of methanol
  6. additionwas added
  7. customcrystallization, and suction filtration
  8. customto obtain crude crystals
  9. temperatureunder reflux
  10. customcrystallization
  11. customobtaining crystals

Sources & evidence

ORD record
ord-e1aa07066ce44a2bbfdd0f9c6f7b1736
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902402B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes