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

HRID 2053547

Reaction equation

HRID 2053547 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:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][Cl:25]>CCO>[ClH:25].[F:19][C:20]([F:29])([F:30])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][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 697163-(Trifluoromethyl)benzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685671332-[(3-Trifluoromethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3-trifluoromethylbenzyl chloride (0.243 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 196 mg of the product 202. 1H NMR (DMSO-d6) δ 11.32 (s, 2H), 8.10-7.65 (m, 4H), 7.15-6.95 (m, 6H), 6.90-6.60 (m, 4H), 5.78 (s, 2H), 4.93 (s, 2H); MS: m/z 413 (M++1).

Workup

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

Sources & evidence

ORD record
ord-3e312cc685954630a0c55a6b2fe23e44
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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