1-Chloro-2-(chloromethyl)-3-fluorobenzene → 2-[(2-Chloro-6-fluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053575Notes

Reaction equation

HRID 2053575 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.[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:21]=1[CH2:22]Cl>CCO>[ClH:19].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[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 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685676152-[(2-Chloro-6-fluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-chloro-6-fluorobenzyl 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 231. 1H NMR (DMSO-d6) δ 11.40 (s, 2H), 7.70-7.30 (m, 3H), 7.25-6.90 (m, 10H), 5.88 (s, 2H), 4.90 (s, 2H); MS: m/z 397 (M++1).

Workup

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

Sources & evidence

ORD record
ord-56cfcbe9778a4f199156dd994941bab4
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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