4-Hydroxybenzoic acid hydrazide → HCID 178515916, compound

HRID 1994012Notes

Reaction equation

HRID 1994012 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-2c7a414a0b4d4564aba2b54d24c9f422
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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