Aniline → HCID 20347054, compound

HRID 1701566Notes

Reaction equation

HRID 1701566 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:13]=[CH:14][CH2:15][CH2:16][CH3:17].[OH-].[Na+]>O.C1C=CC=CC=1>[CH3:13][CH:14]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1])[CH2:15][CH2:16][CH3:17].[CH3:13][CH:14]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH:3]([CH2:2][CH2:7][CH3:6])[CH3:4])[C:2]=1[NH2:1])[CH2:15][CH2:16][CH3:17]

Participants

9

Reactant 5

HCID 6115AnilineHCID 80041-PenteneHCID 14798Sodium HydroxideHCID 5359268AluminumHCID 6451240Aluminum(III) Chloride

Product 2

HCID 20347054HCID 20347054, compoundHCID 23053417HCID 23053417, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

170 g of aniline, 5 g of aluminium granules and 15 g of anhydrous aluminium chloride are heated in a steel autoclave to 300° C. and 300 g of pent-1-ene are pumped in over the course of about 5 hours, until the internal pressure is 300 atmospheres gauge. The batch is then kept at 300° C. for a further 6 hours, in the course of which the internal pressure drops to 107 atmospheres gauge. After it has cooled, the content of the autoclave is stirred with 500 ml of benzene, 250 ml of 40% strength sodium hydroxide solution and 300 ml of water for 15 minutes at 30°-40° C. and the benzene layer is washed with water, dried over potassium carbonate and fractionated. 113 g of 2-mono-pent-2-yl-aniline, boiling point 78°-82° C./0.6 mm Hg, and 131 g of 2,6-bis-pent-2-yl-aniline, boiling point 168°-174° C./1.5 mm Hg are obtained.

Workup

  1. customare pumped in over the course of about 5 hours, until the internal pressure
  2. temperatureAfter it has cooled
  3. washthe benzene layer is washed with water
  4. dry with materialdried over potassium carbonate

Sources & evidence

ORD record
ord-ea3baaf8cd644ba896e29c65c1d7d156
Source dataset
uspto-grants-1980_03
Patent number
US04194008

Reaction notes

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