3,5-Dimethoxybenzyl chloride → 2-[(3,5-Dimethoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053551

Reaktionsgleichung

Reaktionsgleichung von HRID 2053551
[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.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1)[CH2:24][Cl:25]>CCO>[ClH:25].[CH3:30][O:29][C:27]1[CH:26]=[C:23]([CH:22]=[C:21]([O:20][CH3:19])[CH:28]=1)[CH2:24][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 27583953,5-Dimethoxybenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Produkt 1

HCID 685686242-[(3,5-Dimethoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3,5-dimethoxybenzyl chloride (0.293 mg, 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 189 mg of the product 206. 1H NMR (DMSO-d6) δ 11.37 (s, 2H), 7.85-7.45 (m, 4H), 7.20-6.90 (m, 6H), 6.90-6.60 (m, 4H), 5.78 (s, 2H), 4.70 (s, 2H), 3.78 (s, 6H); MS: m/z 405 (M++1).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a78f56debab743bfb8a48c4a26c314d2
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326792B2

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