1-Isothiocyanato-3-(trifluoromethyl)benzene → 1-(2-Phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethyl)-3-(3-(trifluoromethyl)phenyl)thiourea

HRID 238797

Reaktionsgleichung

Reaktionsgleichung von HRID 238797
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:5]=[C:6]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[NH2:11])[CH:7]=[CH:8][CH:9]=1.[N:25]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)=[C:26]=[S:27]>C(Cl)Cl>[C:6]1([CH2:10][C:10]([NH:11][C:26]([NH:25][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:37])[F:36])[CH:29]=2)=[S:27])([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:20])[F:21])[CH:13]=2)[C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:23])([F:24])[F:1])[CH:5]=2)[CH:7]=[CH:8][CH:9]=[CH:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 1372321-Isothiocyanato-3-(trifluoromethyl)benzeneHCID 86613053Bis(3-(trifluoromethoxy)phenyl)methanamine

Produkt 1

HCID 235820971-(2-Phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethyl)-3-(3-(trifluoromethyl)phenyl)thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of bis(3-(trifluoromethoxy)phenyl)methanamine (20 mg, 0.057 mmol) in CH2Cl2 (0.1 mL) was added 1-isothiocyanato-3-(trifluoromethyl)benzene (35 mg, 0.17 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was concentrated and the residue was purified by prep HPLC (phenomenex AXIA Luna 75×30 mm, 5μ column eluting with 10-90% ACN/H2O over 10 minutes containing 0.1% TFA; 40 mL/min, monitoring at 220 nm) to afford 1-(2-phenyl-1,1-bis(3-(trifluoromethoxy)phenyl)ethyl)-3-(3-(trifluoromethyl)phenyl)thiourea (Example 284) as white lyophillate (30 mg, 81%). LCMS: RT=4.51 min [M+H] 645.14 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by prep HPLC (phenomenex AXIA Luna 75×30 mm, 5μ column eluting with 10-90% ACN/H2O over 10 minutes containing 0.1% TFA; 40 mL/min, monitoring at 220 nm)

Quellen und Nachweise

ORD-Eintrag
ord-e790ee04723a40e796890ae32d156ac5
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642576B2

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