1-(Chloromethyl)-2-(trifluoromethyl)benzene → (4S,5R)-4,5-diphenyl-2-[[2-(trifluoromethyl)phenyl]methylsulfanyl]-4,5-dihydro-1H-imidazole;hydrochloride

HRID 18784Notes

Reaction equation

HRID 18784 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:30])([F:29])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][Cl:24]>CCO>[ClH:24].[F:19][C:20]([F:29])([F:30])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[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 890281-(Chloromethyl)-2-(trifluoromethyl)benzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 68568953(4S,5R)-4,5-diphenyl-2-[[2-(trifluoromethyl)phenyl]methylsulfanyl]-4,5-dihydro-1H-imidazole;hydrochlorideYield 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-trifluoromethylbenzyl chloride (0.229 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 224 mg of the product 233. 1H NMR (DMSO-d6) δ 11.41 (s, 2 H), 7.95 (d, 1 H), 7.90-7.75 (m, 2 H), 7.65 (t, 1 H), 7.25-6.90 (m, 10 H), 5.85 (s, 2 H), 4.98 (s, 2 H); MS: m/z 413 (M++1).

Workup

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

Sources & evidence

ORD record
ord-f12847919b034ad8a458811cb4181326
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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