3,4-Dichlorobenzyl chloride → 2-[(3,4-Dichlorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053549

Reaction equation

HRID 2053549 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][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23]Cl>CCO>[ClH:19].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23][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 76093,4-Dichlorobenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685681622-[(3,4-Dichlorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3,4-dichlorobenzyl chloride (0.218 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 217 mg of the product 204. 1H NMR (DMSO-d6) δ 11.40 (s, 2H), 7.95 (d, 1H), 7.78 (d, 1H), 7.65 (d, 1H), 7.20-6.90 (m, 6H), 6.90-6.60 (m, 4H), 5.78 (s, 2H), 4.85 (s, 2H); MS: m/z 413 (M++1).

Workup

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

Sources & evidence

ORD record
ord-4b539126f05048f9a230758d8020158d
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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