4-(Methylsulfanyl)thiophenol → 3-{[4-(Methylsulfanyl)phenyl]sulfanyl}isonicotinaldehyde

HRID 392285

反応式

HRID 392285 の反応式
Cl[C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1>CN(C=O)C>[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:2]2[CH:9]=[N:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:14][CH:13]=1

参加物

4

反応物 2

HCID 1368964-(Methylsulfanyl)thiophenolHCID 27629953-Chloro-4-pyridinecarboxaldehyde

生成物 1

HCID 226639283-{[4-(Methylsulfanyl)phenyl]sulfanyl}isonicotinaldehyde収率 110.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

3-Chloroisonicotinaldehyde [prepared according to R. B. Moffett et al., J. Heterocycl. Chem. 1979, 16, 1459] (550 mg, 3.9 mmol), 4-methylsulfanyl-benzenethiol (732 mg, 4.7 mmol) potassium carbonate (700 mg, 5.1 mmol) and DMF (10 mL) were combined and the mixture was heated together at 65° C. for 2 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was washed with brine, dried (MgSO4) and evaporated to give the title compound (1.124 g) as a yellow oil. The 1H NMR spectrum showed the material to be of sufficient purity (90-95%) to be used without further purification; δH (CDCl3, 300 MHz) 2.52 (3H, s), 7.28 (2H, d), 7.40 (2H, d), 7.64 (1H, d), 8.39 (1H, s), 8.61 (1H, d), 10.42 (1H, s); MS m/z (ES−) 260 (M−H+).

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc (50 mL) and water (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-d290a8cea3ad4fa09adc513686003269
出典データセット
uspto-grants-2004_10
特許番号
US06800652B2

関連ノート

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