N-(Hydroxymethyl)nicotinamide → 4-(3-Picolinoylaminomethylthio)pyridine

HRID 6166ノート

反応式

HRID 6166 の反応式
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.O[CH2:9][NH:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1>FC(F)(F)C(O)=O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([NH:10][CH2:9][S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[O:18])[CH:13]=1

参加物

4

反応物 2

HCID 77116N-(Hydroxymethyl)nicotinamideHCID 178418431pyridine-4-thiol

生成物 1

HCID 539677474-(3-Picolinoylaminomethylthio)pyridine収率 15.9%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To a mixture of 1.11 g (10 mmol) of 4-mercaptopyridine and 1.52 g (10 mmol) of N-(hydroxymethyl)nicotinamide, 30 ml of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off and 30 ml of ethanol was added to the residue. The solvent was distilled off and water was added to the residue. The mixture was neutralized with saturated aqueous sodium bicarbonate, followed by extraction with chloroform. After washing with saturated saline, the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol =5:1) to give 390 mg of the desired compound (15.9% yield, yellow solid).

後処理

  1. additionwas added
  2. distillationThe solvent was distilled off
  3. addition30 ml of ethanol was added to the residue
  4. distillationThe solvent was distilled off
  5. additionwater was added to the residue
  6. extractionfollowed by extraction with chloroform
  7. washAfter washing with saturated saline
  8. dry with materialthe extract was dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was purified by column chromatography (eluent: ethyl acetate/ethanol =5:1)

出典と根拠

ORDレコード
ord-eac925e9b2f940fdb1f04bc16132b520
出典データセット
uspto-grants-1993_09
特許番号
US05246948

反応ノート

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