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 2053578Notes

Reaction equation

HRID 2053578 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, 2H), 7.25-6.95 (m, 10H), 5.85 (s, 2H), 4.84 (s, 2H), 2.38 (s, 6H), 2.20 (s, 9H); MS: m/z 415 (M++1).

Workup

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

Sources & evidence

ORD record
ord-36de0d85a11a4f4584ed5c001e0623d7
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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