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

HRID 18769

Reaction equation

HRID 18769 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:22]=[C:23]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[CH2:24][Cl:25]>CCO>[ClH:25].[CH3:32][O:31][C:27]1[CH:26]=[C:23]([CH:22]=[C:21]([O:20][CH3:19])[C:28]=1[O:29][CH3:30])[CH2:24][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 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685705982-[(3,4,5-Trimethoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 25.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3,4,5-trimethoxybenzyl chloride (0.340 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 93 mg of the product 217. 1H NMR (DMSO-d6) δ 11.10 (m, 2 H), 7.25-6.90 (m, 8 H), 6.90-6.70 (m, 4 H), 5.80 (d, 2 H), 4.70 (s, 1 H), 3.78 (s, 6 H), 3.70 (s, 1 H)

Workup

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

Sources & evidence

ORD record
ord-b6df44aa09c44d48bace16a041a4091b
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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