9-(Chloromethyl)anthracene → 2-[(Anthracen-9-yl)methylthio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18783

Reaction equation

HRID 18783 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][CH2:20][C:21]1[C:22]2[C:27]([CH:28]=[C:29]3[C:34]=1[CH:33]=[CH:32][CH:31]=[CH:30]3)=[CH:26][CH:25]=[CH:24][CH:23]=2>CCO>[ClH:19].[CH:23]1[C:22]2[C:27](=[CH:28][C:29]3[C:34]([C:21]=2[CH2:20][S:18][C:9]2[NH:8][C@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C@H:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:10]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 323859-(Chloromethyl)anthraceneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 865963312-[(Anthracen-9-yl)methylthio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 47.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 9-chloromethylanthracene (256 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 179 mg of the product 232. 1H NMR (DMSO-d6) δ 11.35 (s, 2 H), 8.80 (s, 1 H), 8.64 (d, 2 H), 7.85-7.50 (m, 4 H), 7.38 (d, 1 H), 7.30-6.80 (m, 10 H), 6.80-6.65 (m, 4 H), 5.92 (s, 4 H); MS: m/z 445 (M++1).

Workup

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

Sources & evidence

ORD record
ord-88ac865674fd4376baf499b45cbfd8ae
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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