3-(Chloromethyl)-1,2,4,5-tetramethylbenzene → 2-[(2,3,5,6-Tetramethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18787

Reaktionsgleichung

Reaktionsgleichung von HRID 18787
[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[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[C:24]([CH3:30])[C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[CH3:30][C:24]1[C:25]([CH3:29])=[CH:26][C:27]([CH3:28])=[C:20]([CH3:19])[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 819393-(Chloromethyl)-1,2,4,5-tetramethylbenzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Produkt 1

HCID 865963342-[(2,3,5,6-Tetramethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,3,5,6-tetramethylbenzyl chloride (287 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 236. 1H NMR (DMSO-d6) δ 11.33 (s, 2 H), 7.25-6.95 (m, 11 H), 5.86 (s, 2 H), 4.84 (s, 2 H), 2.35 (s, 6 H), 2.21 (s, 6 H); MS: m/z 401 (M++1).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bc7b54dabd784fa3891319ad36a13c47
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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