Tert-Butylamine → N-tert.butyl-alpha-phenyl-o-toluamide

HRID 46811

Reaktionsgleichung

Reaktionsgleichung von HRID 46811
[C:1]1([CH2:7][C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22]>C(OCC)C.N1C=CC=CC=1>[C:21]([NH:25][C:14]([C:9]1[C:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:16])([CH3:24])([CH3:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 6385Tert-ButylamineHCID 11924o-Benzylbenzoic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 20385869N-tert.butyl-alpha-phenyl-o-toluamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

To a mixture of 49.8 g. (0.235 mole) α-phenyl-o-toluic acid, 300 ml. ether and 10 ml. pyridine, add dropwise with stirring 25 ml. (0.35 mole) of thionyl chloride. The resulting mixture is stirred 21 hours at room temperature then filtered and the solvent removed in vacuo. The resulting acid chloride is dissolved in 150 ml. ether and added dropwise to 35.7 g (0.48 mole) of tert.butylamine in 500 ml. of ethyl ether, and the mixture cooled to 0° C. After addition is complete the resulting mixture is stirred 1 hour at room temperature, the layers separated, the ether washed with 100 ml. of water, 100 ml. of 2 N sodium hydroxide and then with water again, dried over magnesium sulfate, filtered and evaporated to give N-tert.butyl-α-phenyl-o-toluamide; m.p. 91°-92° C.

Aufarbeitung

  1. additionTo a mixture of 49.8 g
  2. stirringThe resulting mixture is stirred 21 hours at room temperature
  3. filtrationthen filtered
  4. customthe solvent removed in vacuo
  5. dissolutionThe resulting acid chloride is dissolved in 150 ml
  6. additionAfter addition
  7. stirringis stirred 1 hour at room temperature
  8. customthe layers separated
  9. washthe ether washed with 100 ml
  10. dry with materialof 2 N sodium hydroxide and then with water again, dried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-79756d4797e94dc0b2b90da49ea04e91
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04175191

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