Diphenylamine → HCID 23067335, compound

HRID 1712231Notes

Reaction equation

HRID 1712231 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]([C:22]4[CH:27]=[CH:26][C:25]([CH:28]=[C:29]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:24][CH:23]=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.[C:42]1([NH:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:49]1([N:48]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:2]2[CH:7]=[CH:6][C:5]([C:8]3[C:9]4[C:14]([C:15]([C:22]5[CH:27]=[CH:26][C:25]([CH:28]=[C:29]([C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=6)[C:30]6[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=6)=[CH:24][CH:23]=5)=[C:16]5[C:21]=3[CH:20]=[CH:19][CH:18]=[CH:17]5)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:4][CH:3]=2)[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

7

Reactant 4

HCID 11487DiphenylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23067332HCID 23067332, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 23067335HCID 23067335, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent3×

Procedure

Under an atmosphere of argon, 9-(4-chlorophenyl)-10-(4-(2,2-diphenylvinyl)phenyl)anthracene (2.4 g, 4.4 mmole), diphenylamine (0.9 g, 5.3 mmole, 1.2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.1 g, 0.11 mmole, 5% Pd), a toluene solution of tri-t-butylphosphine (66% by weight, 0.05 ml, 0.16 mmole, 0.7 eq to Pd) and sodium t-butoxide (0.6 g, 6.3 mmole, 1.4 eq) were suspended in anhydrous toluene (20 ml). The resultant suspension was refluxed for 8 hours. The reaction mixture was filtered and washed with toluene, water and methanol, and a green solid substance was obtained. The obtained solid substance was suspended in boiling toluene (40 ml). After the suspension was cooled while being left standing, the suspension was filtered, and a green solid substance (2.4 g, 81%) was obtained. The result of examination of the obtained product in accordance with 1H-NMR was as follows:

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with toluene, water and methanol
  3. customa green solid substance was obtained
  4. temperatureAfter the suspension was cooled
  5. waitwhile being left standing
  6. filtrationthe suspension was filtered
  7. customa green solid substance (2.4 g, 81%) was obtained
  8. customThe result of examination of the obtained product in accordance with 1H-NMR

Sources & evidence

ORD record
ord-a761b6094dcb40f4b8c0d8ffb2b4f40f
Source dataset
uspto-grants-2010_09
Patent number
US07790892B2

Reaction notes

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