Triethylamine → ethyl 2-(((2,6-dichlorophenyl)thio)methyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate

HRID 2368524Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH2:18]O)=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[Cl:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=1[SH:40].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[Cl:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=1[S:40][CH2:18][C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 1-(4-fluorophenyl)-2-(hydroxymethyl)-1H-imidazole-5-carboxylate (15) (1.25 g, 4.7 mmol) and triethylamine (0.95 g, 9.4 mmol) in CH2Cl2 (30 mL) was added methanesulfonyl chloride (0.65 g, 5.64 mmol) at 0° C. and the reaction was stirred at 0° C. After 3 hours, 2,6-dichlorobenzenethiol (0.84 g mg, 4.7 mmol) and cesium carbonate (2.28 g, 7 mmol) were added and the reaction was stirred at room temperature for 1 hour. The mixture was filtered by vacuum filtration, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford ethyl 2-(((2,6-dichlorophenyl)thio)methyl)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (72).

Workup

stirringthe reaction was stirred at room temperature for 1 hour
filtrationThe mixture was filtered by vacuum filtration
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record: ord-eeb36889033e49a186a801857ce3a5d5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703776B2

Reaction notes

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