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

HRID 247745

Reaktionsgleichung

Reaktionsgleichung von HRID 247745
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 27340052,2,2'-TrimethylpropionanilideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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. (mp 109°-110° C.).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-ba61df26d5534c84b2422beb39b70187
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04709093

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