Pyridine → N-benzyl-N'-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}urea

HRID 131995

Reaktionsgleichung

Reaktionsgleichung von HRID 131995
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:24]([N:31]=[C:32]=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([NH:31][C:32]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[CH:6][CH:7]=1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 76639Benzyl isocyanateHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Produkt 1

HCID 44968109N-benzyl-N'-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}ureaAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Into a 4 mL vial is added 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (75 mg, 0.289 mmol), anhydrous pyridine (1 mL) and benzyl isocyanate (0.036 mL, 0.289 mmol). The reaction mixture was stirred at r.t. for 2 days. To the reaction mixture is added H2O to precipitate the product. The solid is filtered and purified by preparative TLC (MeOH/CHCl3 10:90) to give a colorless solid (84.3 mg, 75%). m.p. 163-164° C. (dec). 1H NMR (DMSO & CHCl3) 4.23 (d, 2H), 6.05 (t, 1H), 7.05 (m, 1H), 7.08 (m, 4H), 7.25 (t, 3H), 7.42 (d, 2H), 8.02 (s, 1H); ESIMS: m/z 393 (M+H).

Aufarbeitung

  1. customto precipitate the product
  2. filtrationThe solid is filtered
  3. custompurified by preparative TLC (MeOH/CHCl3 10:90)

Quellen und Nachweise

ORD-Eintrag
ord-245a48fac34b48daa90291c5d4532eca
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07385063B2

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