4-Hydroxybenzoic acid hydrazide → HCID 178515914, compound

HRID 387445Notes

Reaction equation

HRID 387445 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-10d2c463a0de42d781718dc460ac0b22
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Reaction notes

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