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 2053580

Reaction equation

HRID 2053580 reaction equation
[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

Participants

4

Reactant 2

HCID 819393-(Chloromethyl)-1,2,4,5-tetramethylbenzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 865963342-[(2,3,5,6-Tetramethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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, 2H), 7.25-6.95 (m, 11H), 5.86 (s, 2H), 4.84 (s, 2H), 2.35 (s, 6H), 2.21 (s, 6H); MS: m/z 401 (M++1).

Workup

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

Sources & evidence

ORD record
ord-1f43b8a26a2244a88fb210dbc8603c0d
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

Loading…