Benzene → 1-Phenylazocane

HRID 2248573Notes

Reaction equation

HRID 2248573 reaction equation
[NH2-:1].[Na+].Br[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.C1C=CC=CC=1.[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[N:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:23]1

Participants

6

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 1140TolueneHCID 7961BromobenzeneHCID 24533Sodium amide

Product 1

HCID 152173751-Phenylazocane

Conditions

Temperature
100 °C

Procedure

4.3 g of sodium amide at a concentration of 50% in toluene, suspended in 18.9 cm3 (equivalent to 16.9 g) of heptamethylenamine, are heated to 100° C. for 20 minutes, and 7.85 g (equivalent to 5.03 cm3) of bromobenzene are then added dropwise. The reaction medium is heated to reflux for 18 hours and cooled to room temperature, and 50 cm3 of water are added. 100 cm3 of benzene are added, the organic phase is separated, extracted using 5% strength aqueous hydrochloric acid solution and alkalinized using 20% strength aqueous sodium hydroxide solution, the oil phase is separated, extracted with ethyl ether and dried and the solvent is evaporated off. After distillation of the residue (b.p. 118°-120° C. at 0.5 mm Hg), 9.4 g of expected product are obtained.

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureto reflux for 18 hours
  3. temperaturecooled to room temperature
  4. customthe organic phase is separated
  5. extractionextracted
  6. customthe oil phase is separated
  7. extractionextracted with ethyl ether
  8. customdried
  9. customthe solvent is evaporated off
  10. distillationAfter distillation of the residue (b.p. 118°-120° C. at 0.5 mm Hg), 9.4 g of expected product
  11. customare obtained

Sources & evidence

ORD record
ord-6b8b6e8e16714a46833e8f0f4c51f54f
Source dataset
uspto-grants-1991_08
Patent number
US05041436

Reaction notes

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