4-(Trifluoromethoxy)benzoic acid hydrazide → HCID 178516246, compound

HRID 661406Notes

Reaction equation

HRID 661406 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:10][NH2:11])=O)=[CH:6][CH:5]=1.I.CS[C:19](=[NH:28])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1>N1C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]2[NH:28][C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[N:11][N:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 27772304-(Trifluoromethoxy)benzoic acid hydrazideHCID 178504017HCID 178504017, compound

Product 1

HCID 178516246HCID 178516246, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-trifluoromethoxybenzoic acid hydrazide (1.1 g, 5.0 mmol) and S-methyl N-[4-hydroxy-phenyl]isothiourea hydroiodide (1.55 g, 5.0 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 aqueous layer was decanted and the resulting residue was purified by silica gel chromatography using 1:1 mixture of ethyl acetate/hexane. Solvent was removed in vacuo to give the title product as a pinkish-grey solid (684.0 mg). 40.6% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours, during which time it
  2. additionpoured
  3. customThe aqueous layer was decanted
  4. customthe resulting residue was purified by silica gel chromatography
  5. addition1:1 mixture of ethyl acetate/hexane
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-2056e679c251450483be3557ce791971
Source dataset
uspto-grants-2011_12
Patent number
US08084618B2

Reaction notes

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