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

HRID 18791

Reaktionsgleichung

Reaktionsgleichung von HRID 18791
[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][C:20]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[CH3:19][C:20]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:21]=1[CH2:22][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 699892,4-Dimethylbenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Produkt 1

HCID 685693642-[(2,4-Dimethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,4-dimethylbenzyl chloride (243 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 177 mg of the product 240. 1H NMR (DMSO-d6) δ 11.18 (s, 2 H), 7.20-6.80 (m, 13 H), 5.80 (s, 2 H), 4.88 (s, 2 H), 2.41 (s, 3H), 2.30 (s, 3 H); MS: m/z 373 (M++1).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-426b75bd52694c4c94179c0c84cc5baf
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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