Benzophenone → N-(Diphenylmethylene)glycine tert-butyl ester

HRID 387415

Reaktionsgleichung

Reaktionsgleichung von HRID 387415
[NH2:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:11]1([C:10](=[N:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 3102BenzophenoneHCID 6101p-Toluenesulfonic acidHCID 151417Glycine tert-butyl ester

Produkt 1

HCID 688171N-(Diphenylmethylene)glycine tert-butyl esterAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

A solution of t-butyl 2-aminoacetate (113.7 g, 866.8 mmol, 1.0 equiv) in toluene (1000 mL) was combined with benzophenone (157.9 g, 866.5 mmol, 1.0 equiv) and 4-methylbenzenesulfonic acid (14.9 g, 86.5 mmol, 0.1 equiv). The resulting solution was heated to reflux overnight. The mixture was then concentrated in vacuo to 600 mL. The mixture was cooled to 15° C. with a water/ice bath. The product precipitated and the solids were collected by filtration. The solids was washed with petroleum ether (5×150 mL) to yield t-butyl 2-(diphenylmethyleneamino)acetate (125 g) as a white solid.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was then concentrated in vacuo to 600 mL
  4. customThe product precipitated
  5. filtrationthe solids were collected by filtration
  6. washThe solids was washed with petroleum ether (5×150 mL)

Quellen und Nachweise

ORD-Eintrag
ord-6ecd3f1a47434f90bf24de5f5ac70dd4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372984B2

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