Benzene, 1-(chloromethyl)-2-fluoro- → 2-[(2-Fluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053555Notes

Reaction equation

HRID 2053555 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.[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[F: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 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685673322-[(2-Fluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-fluorobenzyl chloride (0.187 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 141 mg of the product 210. 1H NMR (DMSO-d6) δ 11.28 (s, 2H), 7.80-7.65 (m, 1H), 7.60-7.40 (m, 1H), 7.40-7.20 (m, 2H), 7.20-7.00 (m, 6H), 7.00-6.80 (m, 4H), 5.80 (s, 2H), 4.85 (s, 2H); MS: m/z 363 (M++1).

Workup

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

Sources & evidence

ORD record
ord-62fb2f4c67874a89b0167e202077a914
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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