4-Hydroxybenzoic acid hydrazide → HCID 178515914, compound

HRID 661399Notes

Reaction equation

HRID 661399 reaction equation
I.CS[C:4](=[NH:16])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1.[OH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([NH:24][NH2:25])=O)=[CH:20][CH:19]=1>N1C=CC=CC=1>[F:13][C:12]([F:15])([F:14])[C:8]1[CH:7]=[C:6]([NH:5][C:4]2[NH:16][C:22]([C:21]3[CH:26]=[CH:27][C:18]([OH:17])=[CH:19][CH:20]=3)=[N:24][N:25]=2)[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 178503994HCID 178503994, compound

Product 1

HCID 178515914HCID 178515914, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

S-methyl N-[3-(trifluoromethyl)phenyl]isothiourea hydroiodide (9.09 g, 25.11 mmol) and 4-hydroxybenzoic acid hydrazide (3.82 g, 25.11 mmol) were suspended in ca. 50 mL of anhydrous pyridine under Ar. The mixture was brought to reflux and refluxed under Ar for 12 hrs. Then the dark-yellow solution was cooled down to ambient temperature and pyridine was removed in vacuo. The resulting reddish-yellow solid was re-dissolved in ca. 50 mL of 4:1 mixture of EtOAc/MeOH, ca. 20 g of silica gel was added and solvent was removed in vacuo. The impregnated silica gel was loaded into 25 g ISCO sample cartridge and the product was purified using ISCO system (solid method, 80 g column, 45 min, 0% to 50% EtOAc gradient in hexane). Solvent was removed in vacuo to give the title product as a white solid (3.83 g). Yield 47.6%.

Workup

  1. temperatureto reflux
  2. temperaturerefluxed under Ar for 12 hrs
  3. custompyridine was removed in vacuo
  4. dissolutionThe resulting reddish-yellow solid was re-dissolved in ca. 50 mL of 4:1 mixture of EtOAc/MeOH, ca. 20 g of silica gel
  5. additionwas added
  6. customsolvent was removed in vacuo
  7. customthe product was purified
  8. customISCO system (solid method, 80 g column, 45 min, 0% to 50% EtOAc gradient in hexane)
  9. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-4c906104986a4c74b8266a8370d6a625
Source dataset
uspto-grants-2011_12
Patent number
US08084618B2

Reaction notes

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