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

HRID 2053583Notes

Reaction equation

HRID 2053583 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.[CH:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][Cl:27])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]>CCO>[ClH:27].[CH:19]([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)([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 749164-Isopropylbenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685707482-[(4-Isopropylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 74.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-isopropylbenzyl chloride (264 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 249 mg of the product 239. 1H NMR (DMSO-d6) δ 11.24 (s, 2H), 7.52 (d, 2H), 7.32 (d, 2H), 7.20-6.90 (m, 6H), 6.90-6.70 (m, 4H), 5.77 (s, 2H), 4.78 (s, 2H), 3.02-3.85 (m, 1H), 1.22 (d, 6H); MS: m/z 387 (M++1).

Workup

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

Sources & evidence

ORD record
ord-d3977183eb964dc28870ffeadf4c039c
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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