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

HRID 392285노트

반응식

HRID 392285 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-d290a8cea3ad4fa09adc513686003269
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800652B2

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