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

HRID 2053583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053583
[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.[CH:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][Cl:27])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]>CCO>[ClH:27].[CH:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][S:18][C:9]2[NH:8][C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:10]=2)=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

Komponenten

4

Edukt 2

HCID 749164-Isopropylbenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Produkt 1

HCID 685707482-[(4-Isopropylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-isopropylbenzyl chloride (264 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 249 mg of the product 239. 1H NMR (DMSO-d6) δ 11.24 (s, 2H), 7.52 (d, 2H), 7.32 (d, 2H), 7.20-6.90 (m, 6H), 6.90-6.70 (m, 4H), 5.77 (s, 2H), 4.78 (s, 2H), 3.02-3.85 (m, 1H), 1.22 (d, 6H); MS: m/z 387 (M++1).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d3977183eb964dc28870ffeadf4c039c
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326792B2

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