Ammonia → 2,3,5-Trimethylaniline

HRID 1414438Notes

Reaction equation

HRID 1414438 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1S([O-])(=O)=O.[Na+].[NH2-:15].[Na+].N>>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[NH2:15]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24533Sodium amideHCID 23690032HCID 23690032, compound

Product 1

HCID 127824082,3,5-TrimethylanilineYield 78.8%

Procedure

In a 200-ml autoclave were placed 11.2 grams (0.05 mole) of anydrous sodium 2,3,5-trimethylbenzene sulfonate, 5.2 grams (0.13 mole) of sodium amide and 60 ml liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 160° C for 9 hours. The reaction pressure in the autoclave was 140 atm. during the reaction. After the ammonia was removed, 10 ml of water was added to the reaction mixture for hydrolysis. The product was extracted with ether and the ether was distilled off to produce crude 2,3,5-trimethyl aniline. The recrystallization thereof from petroleum ether gave 5.3 grams of 2,3,5-trimethyl aniline having a melting point of 36° C. Yield was 78.8%.

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed
  4. addition10 ml of water was added to the reaction mixture for hydrolysis
  5. extractionThe product was extracted with ether
  6. distillationthe ether was distilled off
  7. customto produce crude 2,3,5-trimethyl aniline
  8. customThe recrystallization

Sources & evidence

ORD record
ord-7694ccfcbffc45b59bceccec565bd5ef
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

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