Sodium Methoxide → HCID 178506179, compound

HRID 973958Notes

Reaction equation

HRID 973958 reaction equation
C[O-].[Na+].[NH2:4][C:5](=[S:27])[NH:6][NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1>CO>[F:23][C:22]([F:25])([F:24])[C:18]1[CH:17]=[C:16]([NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]2[NH:4][C:5](=[S:27])[NH:6][N:7]=2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 156786042-[(3-Trifluoromethylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide

Product 1

HCID 178506179HCID 178506179, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (548.0 mg, 10.5 mmol) is added to a solution of 2-[(3-trifluoromethylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide (1.023 g, 2.89 mmol) in 50 ml of methanol and the mixture is heated at reflux under a nitrogen atmosphere. Additional amounts of sodium methoxide (548.0 mg and 250.0 mg) are added after heating at reflux for one and two days. The volatiles are removed in vacuo and the residue dissolved in water. The aqueous solution is acidified to pH 4-5 with 1N hydrochloric acid. The resultant pale yellow solid is collected to give 934.1 mg. The solid is chromatographed, eluting with hexane:ethyl acetate (1:2) to give 580.0 mg (59%) of 5-[2-[(3-trifluoromethylphenyl)amino]phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, mp 275°-279° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux under a nitrogen atmosphere
  3. temperatureafter heating
  4. temperatureat reflux for one and two days
  5. customThe volatiles are removed in vacuo
  6. dissolutionthe residue dissolved in water
  7. customThe resultant pale yellow solid is collected
  8. customto give 934.1 mg
  9. customThe solid is chromatographed
  10. washeluting with hexane:ethyl acetate (1:2)

Sources & evidence

ORD record
ord-89edec21fb914bb29c517b91c6ee4bb0
Source dataset
uspto-grants-1991_11
Patent number
US05066668

Reaction notes

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