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

HRID 2053567Notes

Reaction equation

HRID 2053567 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][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][Cl:26])=[CH:23][CH:22]=1>CCO>[ClH:26].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][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:23][CH:22]=1

Participants

4

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685697992-[(4-Methoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 51.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-methoxybenzyl chloride (0.213 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 167 mg of the product 223. 1H NMR (DMSO-d6) δ 11.24 (s, 2H), 7.50 (d, 2H), 7.20-6.90 (m, 8H), 6.90-6.65 (m, 4H), 5.78 (s, 2H), 4.78 (s, 2H), 3.78 (s, 3H); MS: m/z 375 (M++1).

Workup

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

Sources & evidence

ORD record
ord-793aeb04be9c4643a0fee6e13665a040
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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