Sodium Hydroxide → HCID 19025448, compound

HRID 1030974Notes

Reaction equation

HRID 1030974 reaction equation
[CH2:1]([Li])CCC.[F:6][C:7]([F:25])([F:24])[C:8]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([CH3:21])=O)[CH:14]=2)[C:11](=[S:22])[N:10]([CH3:23])[N:9]=1.[OH-].[Na+]>CCCCCC.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[F:6][C:7]([F:25])([F:24])[C:8]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([CH3:1])=[CH2:21])[CH:14]=2)[C:11](=[S:22])[N:10]([CH3:23])[N:9]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 19025438HCID 19025438, compoundHCID 178418339Butyllithium

Product 1

HCID 19025448HCID 19025448, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Under a dry nitrogen atmosphere 23.8 ml of a 1.55M solution of n-butyllithium in hexane was added dropwise to a stirred solution of 15.8 g (0.0443 mole) of methyltriphenylphosphonium bromide in 300 ml of dry tetrahydrofuran. This mixture was stirred at room temperature for 2.5 hours, and a solution of 11.1 g of the oil from Step B in 50 ml of tetrahydrofuran was added dropwise. After complete addition, the reaction mixture was heated at reflux for 2.5 hours. The mixture was cooled to room temperature and was poured into 300 ml of an aqueous, 2N sodium hydroxide solution. This mixture was extracted with 300 ml of diethyl ether. The organic extract was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure, leaving a residue. This residue was purified by column chromatography on silica gel eluting with ethyl acetate: n-heptane (25:75) to yield 3.7 g of 3-trifluoromethyl-4,5-dihydro-1-methyl-4-[3-(1-methylethenyl)phenyl]-1,2,4-triazol-5(1H)-thione as a solid, mp 64°-66° C., Compound 27 of Table 1.

Workup

  1. additionAfter complete addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 2.5 hours
  4. temperatureThe mixture was cooled to room temperature
  5. extractionThis mixture was extracted with 300 ml of diethyl ether
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationwas filtered
  9. customThe filtrate was evaporated under reduced pressure
  10. customleaving a residue
  11. customThis residue was purified by column chromatography on silica gel eluting with ethyl acetate: n-heptane (25:75)

Sources & evidence

ORD record
ord-1439ca0e618a4d09835e6e12d068abc5
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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