O-Toluidine → 2,2,2'-Trimethylpropionanilide

HRID 1462847Notes

Reaction equation

HRID 1462847 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18]>C(Cl)Cl.O>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH3:15]

Participants

6

Reactant 3

HCID 7242O-ToluidineHCID 10340Sodium CarbonateHCID 62493Pivaloyl chloride2×

Product 1

HCID 27340052,2,2'-TrimethylpropionanilideYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A biphasic solution of o-toluidine (107.2 g, 1.0 mol) in methylene chloride (500 ml) and water (150 ml) containing sodium carbonate (69 g, 0.65 mol) was treated with trimethylacetyl chloride (120.6 g, 1.0 mol). The rate of addition of trimethylacetyl chloride was adjusted so as to maintain the reaction at gentle reflux. After 45 minutes the addition was complete. The organic layer was separated, washed with water, and concentrated in vacuo. The crude N-[(2-methyl)phenyl]-2,2-dimethylpropanamide was slurried in 2% aqueous HCl, filtered and washed with H2O until the filtrate was neutral. After drying in vacuo (50° C., 20 mm), N-[(2-methyl)phenyl]-2,2-dimethylpropanamide (178 g, 0.93 mol) was obtained in 93% yield (m.p. 109°-110° C).

Workup

  1. temperatureto maintain
  2. customthe reaction at gentle reflux
  3. additionAfter 45 minutes the addition
  4. customThe organic layer was separated
  5. washwashed with water
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered
  8. washwashed with H2O until the filtrate
  9. customAfter drying in vacuo (50° C., 20 mm)

Sources & evidence

ORD record
ord-5511d4c13407449685b00f28cfcb8f74
Source dataset
uspto-grants-1984_07
Patent number
US04461728

Reaction notes

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