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

HRID 2053561Notes

Reaction equation

HRID 2053561 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, 2H), 7.75 (d, 2H), 7.45 (d, 2H), 7.20-6.90 (m, 6H), 6.90-6.60 (m, 4H), 5.79 (s, 2H), 4.85 (s, 2H); MS: m/z 429 (M++1).

Workup

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

Sources & evidence

ORD record
ord-bbc3745b776945f5bd31ad65440bb8a9
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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