Hydrazinecarboxaldehyde → 2-Methoxy-5-(5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid

HRID 2230741

反応式

HRID 2230741 の反応式
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N:10]=[C:11]=[S:12])[CH:7]=[CH:6][C:5]=1[O:13][CH3:14].[CH:16]([NH:18][NH2:19])=O>O1CCCC1>[CH3:14][O:13][C:5]1[CH:6]=[CH:7][C:8]([N:10]2[C:11](=[S:12])[NH:19][N:18]=[CH:16]2)=[CH:9][C:4]=1[C:3]([OH:2])=[O:15]

参加物

4

反応物 2

HCID 12229HydrazinecarboxaldehydeHCID 18464541Methyl5-isothiocyanato-2-methoxybenzoate

生成物 1

HCID 184646542-Methoxy-5-(5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid収率 91.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Treat a mixture of 5-isothiocyanato-2-methoxy-benzoic acid methyl ester (6.90 g, 30.91 mmol) and formic hydrazide (2.04 g, 34.0 mmol, Aldrich Chemical Company) under an argon atmosphere via syringe with anhydrous tetrahydrofuran (40 mL). After three hours, concentrate in vacuo to remove the solvent, mix the residue with 1 M NaHCO3 solution (total of 300 mL employed) in portions and transfer to a 500 mL round bottom flask. Reflux for 3 days under an argon atmosphere. Filter the hot solution, acidify with concentrated hydrochloric acid (25 mL), chill the mixture in an ice bath and collect the precipitate by vacuum filtration. Wash the filter cake with dichloromethane and dry in vacuo to afford 7.12 g of 2-methoxy-5-(5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid. Combine the filtrates and concentrate in vacuo to afford another crop of 2-methoxy-5-(5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid (1.24 g).

後処理

  1. additionTreat
  2. concentrationconcentrate in vacuo
  3. customto remove the solvent
  4. additionmix the residue with 1 M NaHCO3 solution (total of 300 mL employed) in portions and transfer to a 500 mL round bottom flask
  5. temperatureReflux for 3 days under an argon atmosphere
  6. filtrationFilter the hot solution
  7. temperaturechill the mixture in an ice bath
  8. customcollect the precipitate
  9. filtrationby vacuum filtration
  10. washWash the filter cake with dichloromethane
  11. customdry in vacuo

出典と根拠

ORDレコード
ord-c5ba96bdb174474cb60a73c74263154d
出典データセット
uspto-grants-2002_07
特許番号
US06423704B1

関連ノート

読み込み中…