Flufenamic Acid → HCID 15678604, compound

HRID 2211179Notes

Reaction equation

HRID 2211179 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)=[C:5]([C:7](O)=[O:8])[CH:6]=1.[NH2:21][NH:22][C:23]([NH2:25])=[S:24]>O1CCCC1.N1C=CC=CC=1>[NH2:25][C:23](=[S:24])[NH:22][NH:21][C:7](=[O:8])[C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=1[NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1

Participants

5

Reactant 2

HCID 3371Flufenamic AcidHCID 2723789Thiosemicarbazide

Product 1

HCID 15678604HCID 15678604, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

N,N'-Carbonyldiimidazole (4.56 g, 27.6 mmoles) is added to a room temperature solution of flufenamic acid (5.07 g, 18.0 mmoles) in 70 ml of tetrahydrofuran. The clear yellow solution is stirred at room temperature for three hours. The solution is then added via cannula to a suspension of thiosemicarbazide (3.41 g, 37.5 mmoles) in 55 ml of pyridine. The suspension is heated at reflux overnight. The clear orange solution is concentrated in vacuo, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with additional water, dried over magnesium sulfate, and concentrated. The resulting solid is slurried with a 1:3 mixture of ethyl acetate and hexane. The off-white solid is collected by filtration providing 2.80 g (44%) of 2-[(3-trifluoromethylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide.

Workup

  1. temperatureThe suspension is heated
  2. temperatureat reflux overnight
  3. concentrationThe clear orange solution is concentrated in vacuo
  4. customthe residue is partitioned between ethyl acetate and water
  5. washThe organic layer is washed with additional water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. additionThe resulting solid is slurried with a 1:3 mixture of ethyl acetate and hexane
  9. filtrationThe off-white solid is collected by filtration

Sources & evidence

ORD record
ord-5b7b7ed4bdd34e7583b1e0bcefe756e5
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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