alpha-Chloro-o-xylene → 2-[(2-Methylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18778

Reaction equation

HRID 18778 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[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[CH3:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][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 11093alpha-Chloro-o-xyleneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685671662-[(2-Methylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-methylbenzyl chloride (0.204 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 174 mg of the product 227. 1H NMR (DMSO-d6) δ 11.28 (s, 2 H), 7.68 (m, 1 H), 7.55-7.20 (m, 3 H), 7.20-7.00 (m, 6 H), 7.00-6.90 (m, 4 H), 5.82 (s, 2 H), 4.81 (s, 2 H), 2.44 (s, 3 H); MS: m/z 359 (M++1).

Workup

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

Sources & evidence

ORD record
ord-72cd2c4e099f47c8b31ac4d7f85f95f4
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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