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

HRID 2053573Notes

Reaction equation

HRID 2053573 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]=[C:26]([F:28])[CH:25]=[CH:24][C:21]=1[CH2:22]Cl>CCO>[ClH:19].[Cl:19][C:20]1[CH:27]=[C:26]([F:28])[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 27250642-Chloro-1-(chloromethyl)-4-fluorobenzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685707522-[(2-Chloro-4-fluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 73.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-chloro-4-fluorobenzyl chloride (281 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 249 mg of the product 229. 1H NMR (DMSO-d6) δ 11.35 (s, 2H), 8.00-7.80 (m, 1H), 7.75-7.60 (m, 1H), 7.55-7.35 (m, 1H), 7.20-7.00 (m, 6H), 7.00-6.85 (m, 4H), 5.80 (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-a1fe91dcd8ce42a884957a1e1522376e
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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