Pyridinium chloride → HCID 19025434, compound

HRID 1030976Notes

Reaction equation

HRID 1030976 reaction equation
Cl.N1C=CC=CC=1.C([O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21](=[S:22])[N:20]([CH3:23])[N:19]=[C:18]2[C:24]([F:27])([F:26])[F:25])=[CH:13][CH:12]=1)C>O>[F:26][C:24]([F:25])([F:27])[C:18]1[N:17]([C:14]2[CH:13]=[CH:12][C:11]([OH:10])=[CH:16][CH:15]=2)[C:21](=[S:22])[N:20]([CH3:23])[N:19]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 19025436HCID 19025436, compound

Product 1

HCID 19025434HCID 19025434, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
215 °C

Procedure

A mixture of 12.6 g (0.109 mole) of pyridine hydrochloride and 11.0 g (0.0363 mole) of 4-(4-ethoxyphenyl)-3-trifluoromethyl-4,5-dihydro-1-methyl-1,2,4-triazol-5(1H)-thione was heated at 215° C. and stirred for one hour. The mixture was cooled and dissolved in water. The aqueous solution was extracted with a mixture of tetrahydrofuran:diethyl ether (50:50). The organic phase was extracted with an aqueous, 10% sodium hydroxide solution. The basic extract was acidified, forming a precipitate. This solid was collected by filtration and dried to yield 7.1 g of 3-trifluoromethyl-4,5-dihydro-4-(4-hydroxyphenyl)-1-methyl-1,2,4-triazol-5(1H)-thione, mp 150°-152° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe aqueous solution was extracted with a mixture of tetrahydrofuran:diethyl ether (50:50)
  3. extractionThe organic phase was extracted with an aqueous, 10% sodium hydroxide solution
  4. extractionThe basic extract
  5. customforming a precipitate
  6. filtrationThis solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-7a60448a3fca4cc1a5e7a45eb38d4de7
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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