Diphenylamine → HCID 9794962, compound

HRID 1282479Notes

Reaction equation

HRID 1282479 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.BrC1SC=CC=1.[C:13]1([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+].C1(C(C2C=CC=CC=2)=C(P(C2CCCCC2)C2CCCCC2)C)C=CC=CC=1.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[S:4]1[CH:5]=[CH:6][C:2]([N:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3]1

Participants

9

Reactant 6

HCID 11487DiphenylamineHCID 133833-BromothiopheneHCID 138512-BromothiopheneHCID 25517Ammonium ChlorideHCID 12010824Cy-vBRIDPHCID 23676156Sodium t-butoxide

Product 1

HCID 9794962HCID 9794962, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Into a reactor were introduced 0.358 g (2.20 mmol) of 3-bromothiophene and 4 mL of toluene under a nitrogen atmosphere. The bromothiophene was dissolved in the solvent. To this solution were added 0.343 g (2.03 mmol) of diphenylamine, 0.229 g (2.39 mmol) of sodium t-butoxide, 4.4 mg (1 mol % based on the amine) of palladium acetate, and 30.6 mg (2 mmol % based on the amine) of the 1,1-diphenyl-2-(dicyclohexylphosphino)propene obtained in Example 2. The resultant reaction mixture was stirred at 100° C. for 10 hours and then cooled. Saturated aqueous ammonium chloride solution was added thereto, and this mixture was extracted with toluene. The extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was purified by column chromatography to obtain 0.257 g (50%) of N-(3-thiophenyl)-N,N-diphenylamine. The results obtained are shown in Table 20.

Workup

  1. customThe resultant reaction mixture
  2. temperaturecooled
  3. extractionthis mixture was extracted with toluene
  4. dry with materialThe extract was dried with anhydrous magnesium sulfate
  5. customThereafter, the solvent was removed under reduced pressure
  6. customThe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-bbf995be8d5044baaca4f35749e2934e
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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