Diphenylamine → HCID 23067343, compound

HRID 1712232Notes

Reaction equation

HRID 1712232 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]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[C:24]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[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:40]1([NH:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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:47]1([N:46]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=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]([C:28]6[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=6)=[C:24]([C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=6)[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:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

7

Reactant 4

HCID 11487DiphenylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23067338HCID 23067338, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 23067343HCID 23067343, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent3×

Procedure

Under an atmosphere of argon, 9-(4-chlorophenyl)-10-(3,4-diphenylphenyl)anthracene (2.3 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 mixture was refluxed for 8 hours. The reaction mixture was filtered and washed with toluene, water and methanol, and a light yellow 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 light yellow solid substance (2.2 g, the yield: 78%) was obtained. It was confirmed in accordance with 1H-NMR and FDMS that the obtained product was Compound (A11).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with toluene, water and methanol
  3. customa light yellow solid substance was obtained
  4. temperatureAfter the suspension was cooled
  5. waitwhile being left standing
  6. filtrationthe suspension was filtered
  7. customa light yellow solid substance (2.2 g, the yield: 78%) was obtained

Sources & evidence

ORD record
ord-27cda8f5cc4048f0aeda421ada8600df
Source dataset
uspto-grants-2010_09
Patent number
US07790892B2

Reaction notes

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