Benzyl mercaptan → HCID 22118831, compound

HRID 1274902Notes

Reaction equation

HRID 1274902 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:12][C:11](=O)[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[N:9][N:8]=1.S(Cl)(Cl)=O.[C:28]1([CH2:34][SH:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C(Cl)Cl.O1CCCC1>[CH2:34]([S:35][C:11]1[N:12]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:8]=[N:9][C:10]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1354183873-(2-Pyridinyl)-6-[4-(trifluoromethyl)phenyl]-1,2,4-triazin-5(2H)-one

Product 1

HCID 22118831HCID 22118831, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(2-pyridyl)-6-(4-trifluoromethylphenyl)-1,2,4-triazin-5-one (200 mg, 0.63 mmol) and thionyl chloride (5 ml) was heated under reflux for 30 minutes. The mixture was allowed to cool to room temperature, and the solvent was distilled off. To the residue were added tetrahydrofuran (4 ml), phenyl methanethiol (195 mg, 1.57 mmol, 2.5 eq.), and triethylamine (159 mg, 1.57 mmol, 2.5 eq.), and the mixture was stirred at room temperature for one hour. To the reaction mixture was added methylene chloride (50 ml), and the mixture was washed with water (20 ml), a saturated aqueous sodium hydrogen carbonate solution (20 ml) and a saturated brine (20 ml). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to remove the solvent. The resulting solid was purified by flash silica gel column chromatography (chloroform) to give the title compound (248 mg, 93%) as pale yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. distillationthe solvent was distilled off
  4. washthe mixture was washed with water (20 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customThe resulting solid was purified by flash silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-416caf31e35740dcb5e6f20e3c9f6092
Source dataset
uspto-grants-2000_12
Patent number
US06159974

Reaction notes

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