Toluene → HCID 23498331, compound

HRID 1836073Notes

Reaction equation

HRID 1836073 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C1(C)C=CC=CC=1.[NH2-].[Na+]>O>[CH2:15]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 1140TolueneHCID 81011-BromohexaneHCID 11487DiphenylamineHCID 24533Sodium amide

Product 1

HCID 23498331HCID 23498331, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

253.8 Grams of diphenylamine, 297.0 g of 1-bromohexane and 1,500 ml of toluene were mixed, and 150 g of sodiumamide was added little by little with stirring. After completion of the addition, the mixture was refluxed under heat on an oil bath at 120° C. with stirring for 10 hours. Then, the reaction mixture was poured into 2,000 ml of water little by little, and the mixture was stirred at room temperature for 1.0 hours. During the stirring, heat generation was observed. The mixture was transferred into a separation funnel, and an organic layer was recovered. The recovered liquid was washed consecutively with water and saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The resultant oily substance was distilled under reduced pressure, to give 337 g of N-hexyldiphenylamine (117) having a boiling point of 173-175° C. (0.4 Torr). The yield thereof was 88.6%.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was refluxed
  3. stirringwith stirring for 10 hours
  4. stirringwas stirred at room temperature for 1.0 hours
  5. temperatureDuring the stirring, heat generation
  6. customThe mixture was transferred into a separation funnel
  7. customan organic layer was recovered
  8. washThe recovered liquid was washed consecutively with water and saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe resultant oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-5faaec7ab4ed431f8219d92cf0295268
Source dataset
uspto-grants-2004_08
Patent number
US06777148B2

Reaction notes

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