1-Chloromethylnaphthalene → 2-[(Naphthalen-1-yl)methylthio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053558Notes

Reaction equation

HRID 2053558 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.[Cl:19][CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>CCO>[ClH:19].[C:21]1([CH2:20][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)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 68451-ChloromethylnaphthaleneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685711322-[(Naphthalen-1-yl)methylthio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 19.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 1-chloromethylnaphthalene (0.277 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 67 mg of the product 213. 1H NMR (DMSO-d6) δ 11.20 (s, 2H), 8.40-8.25 (m, 1H), 8.10-7.90 (m, 2H), 7.90-7.80 (m, 1H), 7.80-7.50 (3, H), 7.20-6.70 (m, 10H), 5.79 (s, 2H), 4.85 (s, 2H); MS: m/z 395 (M++1).

Workup

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

Sources & evidence

ORD record
ord-41bc200e638e4dc1a2c44ee2e199a962
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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