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

HRID 2053574

Reaktionsgleichung

Reaktionsgleichung von HRID 2053574
[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]=[CH:26][C:25]([CH3:28])=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[CH3:19][C:20]1[CH:27]=[CH:26][C:25]([CH3:28])=[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 69987Benzene, 2-(chloromethyl)-1,4-dimethyl-HCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Produkt 1

HCID 685692182-[(2,5-Dimethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,5-dimethylbenzyl chloride (0269 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 171 mg of the product 230. 1H NMR (DMSO-d6) δ 11.20 (s, 2H), 7.38 (s, 1H), 7.30-7.00 (m, 8H), 7.00-6.85 (m, 4H), 5.82 (s, 2H), 4.75 (s, 2H), 2.40 (s, 3H), 2.30 (s, 3H); MS: m/z 373 (M++1).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8282826e26fe4eaf81ec198ff6e46a00
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326792B2

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