1-(Chloromethyl)-2-iodobenzene → 2-[(2-Iodobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053566Notes

Reaction equation

HRID 2053566 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.[I:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[I: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 1010641-(Chloromethyl)-2-iodobenzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685694252-[(2-Iodobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 67.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-iodobenzyl chloride (396 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 270 mg of the product 222. 1H NMR (DMSO-d6) δ 11.43 (s, 2H), 8.00 (d, 1H), 7.82 (d, 1H), 7.48 (t, 1H), 7.30-7.00 (m, 7H), 7.00-6.80 (m, 4H), 5.82 (s, 2H), 4.88 (s, 2H); MS: m/z 471 (M++1).

Workup

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

Sources & evidence

ORD record
ord-a9f4865131114d46aba6d2bc67b50696
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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