1-(Chloromethyl)-2-(trifluoromethyl)benzene → (4S,5R)-4,5-diphenyl-2-[[2-(trifluoromethyl)phenyl]methylsulfanyl]-4,5-dihydro-1H-imidazole;hydrochloride

HRID 18784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18784
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][C:9](=[S:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][Cl:24]>CCO>[ClH:24].[F:19][C:20]([F:29])([F:30])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][S:18][C:9]1[NH:8][C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1

Komponenten

4

Edukt 2

HCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Produkt 1

HCID 68568953(4S,5R)-4,5-diphenyl-2-[[2-(trifluoromethyl)phenyl]methylsulfanyl]-4,5-dihydro-1H-imidazole;hydrochlorideAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-trifluoromethylbenzyl chloride (0.229 mL, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 224 mg of the product 233. 1H NMR (DMSO-d6) δ 11.41 (s, 2 H), 7.95 (d, 1 H), 7.90-7.75 (m, 2 H), 7.65 (t, 1 H), 7.25-6.90 (m, 10 H), 5.85 (s, 2 H), 4.98 (s, 2 H); MS: m/z 413 (M++1).

Aufarbeitung

  1. customevaporated to dryness
  2. filtrationThe insoluble material is filtered

Quellen und Nachweise

ORD-Eintrag
ord-f12847919b034ad8a458811cb4181326
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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