Sodium Carbonate → Ethyl (1,2-diphenylethyl)carbamate

HRID 2351103

Reaktionsgleichung

Reaktionsgleichung von HRID 2351103
[C:1]1([CH:7]([NH2:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(Cl)Cl.O>[C:23]([NH:15][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([O:25][CH2:26][CH3:27])=[O:24]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 264821,2-Diphenylethylamine

Produkt 1

HCID 234956Ethyl (1,2-diphenylethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a stirred two phase solution of 1,2-diphenylethylamine (30.0 g, 0.15 mol) in 300 ml of methylene chloride and 500 ml of water was added sodium carbonate (23.9 g, 0.225 mol) and the solution was cooled to 10° C. under nitrogen. Ethyl chloroformate (21.5 ml, 0.225 mol) was added dropwise over a one hour period. The reaction was warmed to ambient temperature and stirred at that temperature for 3 hours. The phases were separated and the aqueous phase was extracted with methylene chloride (75 ml). The combined methylene chloride extracts were washed with 1N HCl (200 ml), brine (200 ml), dried and evaporated to a white solid, 40.3 g. Recrystallization from cyclohexane gave N-carboethoxy-1,2-diphenylethylamine, mp 74°-75° C.

Aufarbeitung

  1. temperatureThe reaction was warmed to ambient temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with methylene chloride (75 ml)
  4. washThe combined methylene chloride extracts were washed with 1N HCl (200 ml), brine (200 ml)
  5. customdried
  6. customevaporated to a white solid, 40.3 g
  7. customRecrystallization from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-c83238845a544833a269c3348ebf4ddf
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04871872

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