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

HRID 18763

Reaction equation

HRID 18763 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[CH:27]=[CH:26][C:23]([CH2:24][Cl:25])=[CH:22][CH:21]=1>CCO>[ClH:25].[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][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:22][CH:21]=1

Participants

4

Reactant 2

HCID 77224-Methylbenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685708292-[(4-Methylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-methylbenzyl chloride (0.208 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 199 mg of the product 211. 1H NMR (DMSO-d6) δ 11.18 (s, 2 H), 7.45 (d, 2 H), 7.25 (d, 2 H), 7.20-6.90 (m, 6 H), 6.90-6.65 (m, 4 H), 5.77 (s, 2 H), 4.73 (s, 2 H), 2.35 (s, 3 H); MS: m/z 359 (M++1).

Workup

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

Sources & evidence

ORD record
ord-9e5bc21144d9447e8d3929769ecbd73f
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

Loading…