4-Hydroxybenzoic acid hydrazide → HCID 178515916, compound

HRID 661395Notes

Reaction equation

HRID 661395 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=O)=[CH:4][CH:3]=1.I.CS[C:15](=[NH:28])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:25][C:24]([F:26])([F:27])[O:23][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:15]2[NH:28][C:6]([C:5]3[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=3)=[N:8][N:9]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 178504018HCID 178504018, compound

Product 1

HCID 178515916HCID 178515916, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-hydroxybenzoic acid hydrazide (0.643 g, 4.23 mmol) and S-methyl N-[4-(trifluoromethoxy)phenyl]isothiourea hydroiodide (1.6 g, 4.23 mmol) were suspended in 10 mL of anhydrous pyridine. The reaction mixture was refluxed for 24 hours, during which time it changed color from yellow into orange-red. Then it was cooled down to ambient temperature and poured with stirring into 150 mL of ice-water. The formed white solid was collected, washed thoroughly with water and dried in air. The resulting residue was purified by silica gel chromatography using Isco column with 10% to 100% gradient of ethyl acetate in hexane. Solvent was removed in vacuo to give the title product as a pinkish solid (575.2 mg). Yield 40.4%.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours, during which time it
  2. additionpoured
  3. customThe formed white solid was collected
  4. washwashed thoroughly with water
  5. customdried in air
  6. customThe resulting residue was purified by silica gel chromatography
  7. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-8d4880fc028745369463d1c05d2702eb
Source dataset
uspto-grants-2011_12
Patent number
US08084618B2

Reaction notes

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