Triethylamine → (R)-1-Benzoyl-3-(1-methyl-2,2,2-trifluoroethyl)-thiourea

HRID 1191078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191078
Cl.[CH3:2][C@@H:3]([NH2:8])[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)(Cl)Cl>[C:16]([NH:24][C:25]([NH:8][C@H:3]([CH3:2])[C:4]([F:7])([F:6])[F:5])=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 68284Benzoyl isothiocyanateHCID 44593757(R)-2-Amino-1,1,1-trifluoropropane hydrochloride

Produkt 1

HCID 58495475(R)-1-Benzoyl-3-(1-methyl-2,2,2-trifluoroethyl)-thioureaAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve (R)-1-methyl-2,2,2-trifluoroethylamine hydrochloride (3.73 g, 25 mmol) in chloroform (50 mL) containing triethylamine (3.5 mL, 25 mmol). Cool to 0° C. in an ice bath and dropwise add benzoyl isothiocyanate (3.35 mL, 25 mmol) over 10 min. Warm the mixture to room temperature and stir overnight. Concentrate in vacuo and purify by chromatography on silica gel (200 g) eluting with hexane/EtOAc (19:1 to 4:1 over 40 min; 50 mL/min) to afford the desired intermediate as a light yellow oil (6.2 g, 90%).

Aufarbeitung

  1. temperatureWarm the mixture to room temperature
  2. concentrationConcentrate in vacuo
  3. custompurify by chromatography on silica gel (200 g)
  4. washeluting with hexane/EtOAc (19:1 to 4:1 over 40 min; 50 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-01c43b2f15e1481982cab6dbf9c8623c
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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