Benzene, 1-(chloromethyl)-2,3,4,5,6-pentamethyl- → 2-[(2,3,4,5,6-Pentamethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18785Notes

Reaction equation

HRID 18785 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.[CH3:19][C:20]1[C:27]([CH3:28])=[C:26]([CH3:29])[C:25]([CH3:30])=[C:24]([CH3:31])[C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[CH3:22][C:21]1[C:20]([CH3:19])=[C:27]([CH3:28])[C:26]([CH3:29])=[C:25]([CH3:30])[C:24]=1[CH2:31][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 68087Benzene, 1-(chloromethyl)-2,3,4,5,6-pentamethyl-HCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 865963332-[(2,3,4,5,6-Pentamethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 52.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,3,4,5,6-pentamethylbenzyl chloride (309 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 186 mg of the product 234. 1H NMR (DMSO-d6) δ 11.20 (s, 2 H), 7.25-6.95 (m, 10 H), 5.85 (s, 2 H), 4.84 (s, 2 H), 2.38 (s, 6 H), 2.20 (s, 9 H); MS: m/z 415 (M++1).

Workup

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

Sources & evidence

ORD record
ord-48f9ef940ad84c8090a0286dddf466d1
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

Loading…