反応式
[Na].[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:10])[C:8]=1[SH:9].Cl[C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:10])[C:8]=1[S:9][C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22]参加物
実験手順
3,5-dichloropyridine-4-thiol sodium salt prepared as in example 17 (0.179 g, 1 mmol), methyl 5-chloro-4-nitro-thiophene-2-carboxylate (221 mg, 1 mmol) was mixed in toluene (5 mL). Then potassium carbonate (0.207 g, 1.5 mmol) was added. The resulting reaction mixture was stirred at ambient temperature for 4 hours. After this time, the reaction mixture was filtered and diluted with ethyl acetate. The organic solution was washed with water (2 mL×2), brine (2 mL×2), dried (Na2SO4), and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with a 96:4 mixture of hexane and ethyl acetate to afford the title product as a solid (82.5 mg, 23% yield). 1H NMR (300 MHz, d6-DMSO) δ: 9.05 (2H, s), 8.20 (1H, s), 3.82 (3H, s). MS m/z: 365.2 [M+H]+.
後処理
- customThe resulting reaction mixture
- filtrationAfter this time, the reaction mixture was filtered
- additiondiluted with ethyl acetate
- washThe organic solution was washed with water (2 mL×2), brine (2 mL×2)
- dry with materialdried (Na2SO4)
- concentrationconcentrated under vacuum
- customThe residue was purified by silica gel chromatography
- washeluting with a 96:4 mixture of hexane and ethyl acetate
出典と根拠
- ORDレコード
- ord-db302e0579fb4d968464959adf3813fc
- 出典データセット
- uspto-grants-2014_03
- 特許番号
- US08680139B2
関連ノート
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