3,4-Difluorobenzyl Chloride → 2-[(3,4-Difluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053559

Reaction equation

HRID 2053559 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:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23][Cl:24]>CCO>[ClH:24].[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23][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 27369543,4-Difluorobenzyl ChlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685696432-[(3,4-Difluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 63.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3,4-difluorobenzyl chloride (0.255 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 207 mg of the product 214. 1H NMR (DMSO-d6) δ 11.38 (s, 2H), 7.90-7.65 (m, 1H), 7.65-7.40 (m, 2H), 7.20-6.90 (m, 6H), 6.90-6.65 (m, 4H), 5.79 (s, 2H), 4.85 (s, 2H); MS: m/z 381 (M++1).

Workup

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

Sources & evidence

ORD record
ord-f57ff2190632437ab7f03fccfce13154
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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