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

HRID 2230741

반응식

HRID 2230741 반응식
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]

참가 물질

4

반응물 2

HCID 12229HydrazinecarboxaldehydeHCID 18464541Methyl5-isothiocyanato-2-methoxybenzoate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c5ba96bdb174474cb60a73c74263154d
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06423704B1

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