Ammonia → 2,4-Dimethylaniline

HRID 1414442Notes

Reaction equation

HRID 1414442 reaction equation
[C:1]1([CH3:12])[CH:6]=[C:5](S([O-])(=O)=O)[CH:4]=[C:3]([CH3:11])[CH:2]=1.[Na+].[NH2-:14].[Na+].N>>[CH3:12][C:1]1[CH:6]=[CH:5][C:4]([NH2:14])=[C:3]([CH3:11])[CH:2]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24533Sodium amideHCID 5039848HCID 5039848, compound

Product 1

HCID 72502,4-DimethylanilineYield 84.4%

Procedure

In a 200-ml autoclave were placed 22.9 grams (0.11 mole) of anhydrous sodium 5-m-xylene sulfonate, 9.7 grams (0.24 mole) of sodium amide and 80 ml of liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 150° C for 5 hours. The reaction pressure in the autoclave was 135 atm. during the reaction. After the ammonia was removed, 20 ml of water was added to the reaction mixture for hydrolysis. Thereafter the product was treated in the same manner as in Example 1, whereby 11.3 grams of sym. -m-xylidine boiling at 221° to 222° C was obtained. Yield was 84.4%

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed
  4. addition20 ml of water was added to the reaction mixture for hydrolysis
  5. additionThereafter the product was treated in the same manner as in Example 1, whereby 11.3 grams of sym

Sources & evidence

ORD record
ord-85e2173164b7437db830a6d4ba083913
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

Loading…