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

HRID 18750

Reaction equation

HRID 18750 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.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][Cl:25])=[CH:22][CH:21]=1>CCO>[ClH:25].[F: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 96024-Fluorobenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685688872-[(4-Fluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (0.50 g, 1.9 mmol) and 4-fluorobenzyl chloride (0.47 mL, 0.3.93 mmol) in abs. EtOH (20 mL) is heated at 90° 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 0.70 g of the product 197. 1H NMR (DMSO-d6) δ 11.37 (s, 2H), 7.75-7.65 (m, 2 H), 7.40-7.25 (m, 2 H), 7.15-6.95 (m, 6 H), 6.90-6.70 (m, 4 H), 5.78 (s, 2 H), 4.84 (s, 2 H); MS: m/z 363 (M++1).

Workup

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

Sources & evidence

ORD record
ord-3c2b43d2d6734813a99b597a26b8eecf
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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