2-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazide → HCID 178425397, compound

HRID 973956Notes

Reaction equation

HRID 973956 reaction equation
C[O-].[Na+].[NH2:4][C:5](=[S:26])[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[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH3:23])[C:17]=1[Cl:24]>CO>[Cl:24][C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]1[NH:4][C:5](=[S:26])[NH:6][N:7]=1

Participants

4

Reactant 2

HCID 98641092-[(2,6-Dichloro-3-methylphenyl) amino]-benzoic acid, 2-(aminothioxomethyl)hydrazideHCID 10942334Sodium Methoxide2×

Product 1

HCID 178425397HCID 178425397, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (734.0 mg, 13.59 mmol) is added to a solution of 2-[(2,6-dichloro-3-methylphenyl)amino]-benzoic acid, 2-(aminothioxomethyl)-hydrazide (1.466 g, 3.96 mmol) in 60 ml of methanol and the mixture is heated at reflux overnight, under a nitrogen atmosphere. An additional amount of sodium methoxide (702.0 mg, 13.00 mmol) is added and heating at reflux is continued overnight. The volatiles are removed in vacuo and the residue dissolved in water. The aqueous solution is acidified to pH 4-5 with 10% hydrochloric acid. The resultant white solid is collected, dissolved in tetrahydrofuran and chromatographed, eluting with hexane:ethyl acetate (1:2) to give 599.2 mg (43%) of 5-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, mp 300°-305° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight, under a nitrogen atmosphere
  3. temperatureheating
  4. temperatureat reflux
  5. customThe volatiles are removed in vacuo
  6. dissolutionthe residue dissolved in water
  7. customThe resultant white solid is collected
  8. dissolutiondissolved in tetrahydrofuran
  9. customchromatographed
  10. washeluting with hexane:ethyl acetate (1:2)

Sources & evidence

ORD record
ord-5bc840694d93412287f526dfa2fef373
Source dataset
uspto-grants-1991_11
Patent number
US05066668

Reaction notes

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