Iodoethane → HCID 19025411, compound

HRID 1030972Notes

Reaction equation

HRID 1030972 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[S:13])[N:11]([CH3:14])[N:10]=[C:9]2[C:15]([F:18])([F:17])[F:16])=[C:4]([Cl:19])[CH:3]=1.[C:20](#N)[CH3:21].C(=O)(O)[O-].[Na+].I[CH2:29][CH3:30]>O>[Cl:19][C:4]1[CH:3]=[C:2]([N:1]([CH2:20][CH3:21])[CH2:29][CH3:30])[CH:7]=[CH:6][C:5]=1[N:8]1[C:12](=[S:13])[N:11]([CH3:14])[N:10]=[C:9]1[C:15]([F:16])([F:18])[F:17]

Participants

6

Reactant 4

HCID 6340Iodoethane2×HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 19025437HCID 19025437, compound

Product 1

HCID 19025411HCID 19025411, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3.5 g (0.011 mole) of 4-(4-amino-2-chlorophenyl)-3-trifluoromethyl-4,5-dihydro-1-methyl-1,2,4-triazol-5(1H)-thione in a 100 ml of acetonitrile were added in succession 2.9 g (0.034 mole) of sodium bicarbonate and 3.7 g (0.024 mole) of iodoethane. The reaction mixture was heated at reflux for approximately 18 hours. An additional 1.8 g (0.011 mole) of iodoethane was added, and the reaction was stirred at room temperature for two days. The mixture was cooled, and the solvent was evaporated under reduced pressure, leaving a residue. Water was added to the residue, and the mixture was extracted with methylene chloride. 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 to produce two fractions. The first fraction yielded 0.5 g of 4-(2-chloro-4-diethylaminophenyl)-3-trifluoromethyl-4,5-dihydro-1-methyl-1,2,4-triazol-5(1H)-thione as a solid, mp 108°-110° C., Compound 98 of Table 1. The second fraction yielded 1.5 g of 4-(2-chloro-4-ethylaminophenyl)-3-trifluoromethyl-4,5-dihydro-1-methyl-1,2,4-triazol-5(1H)-thione as a solid, mp 87°-90° C., Compound 96 of Table 1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. customleaving a residue
  6. extractionthe mixture was extracted with methylene chloride
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationwas filtered
  10. customThe filtrate was evaporated under reduced pressure
  11. customleaving a residue
  12. customThis residue was purified by column chromatography
  13. customto produce two fractions

Sources & evidence

ORD record
ord-a5a54191fa2b49d18fa59e43ac39bfa7
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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