Triethylamine → N-(3-cyanophenyl)-N'-t-butyloxycarbonylmethylthiourea

HRID 1649859

Reaktionsgleichung

Reaktionsgleichung von HRID 1649859
C(N(CC)CC)C.[C:8]([C:10]1[CH:11]=[C:12]([N:16]=[C:17]=[S:18])[CH:13]=[CH:14][CH:15]=1)#[N:9].[C:19]([O:23][C:24](=[O:27])[CH2:25][NH2:26])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[C:8]([C:10]1[CH:11]=[C:12]([NH:16][C:17]([NH:26][CH2:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:27])=[S:18])[CH:13]=[CH:14][CH:15]=1)#[N:9]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 765783-Cyanophenyl isothiocyanateHCID 151417Glycine tert-butyl ester

Produkt 1

HCID 19855133N-(3-cyanophenyl)-N'-t-butyloxycarbonylmethylthioureaAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

2.8 cm3 (20 mmol) of triethylamine and 3.2 g (20 mmol) of 3-cyanophenyl isothiocyanate are added at 0° C. to a solution of 3.35 g (20 mmol) of glycine t-butyl ester in 150 cm3 of dichloromethane. The mixture is stirred at 20° C. for 12 hours before being concentrated under vacuum and then taken up with a mixture of water and ethyl ether (300:300). The ether phase is separated off and washed with a 1N hydrogen chloride solution (200 cm3), and then with a saturated sodium chloride solution. After drying with magnesium sulfate and concentration under vacuum, 5.17 g (89% yield) of a yellow solid is obtained, whose melting point is 131°-132° C.

Aufarbeitung

  1. concentrationbefore being concentrated under vacuum
  2. additiontaken up with a mixture of water and ethyl ether (300:300)
  3. customThe ether phase is separated off
  4. washwashed with a 1N hydrogen chloride solution (200 cm3)
  5. dry with materialAfter drying with magnesium sulfate and concentration under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a883bce4da3548f6be9b691dcc12b140
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04921939

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