4-(Trifluoromethoxy)benzyl Chloride → 2-[(4-Trifluoromethoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18768

Reaction equation

HRID 18768 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]([F:31])([F:30])[O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][Cl:27])=[CH:24][CH:23]=1>CCO>[ClH:27].[F:19][C:20]([F:30])([F:31])[O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][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:24][CH:23]=1

Participants

4

Reactant 2

HCID 27772614-(Trifluoromethoxy)benzyl ChlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685694812-[(4-Trifluoromethoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 62.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-trifluoromethoxybenzyl chloride (0.331 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 229 mg of the product 216. 1H NMR (DMSO-d6) δ 11.30 (s, 2 H), 7.75 (d, 2 H), 7.45 (d, 2 H), 7.20-6.90 (m, 6 H), 6.90-6.60 (m, 4 H), 5.79 (s, 2 H), 4.85 (s, 2 H); MS: m/z 429 (M++1).

Workup

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

Sources & evidence

ORD record
ord-a0a374ffb69f439dae1ccb8425254a3c
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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