Methyl iodide → HCID 89689483, compound

HRID 514173Notes

Reaction equation

HRID 514173 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[CH2:7]([Li])CCC.CI.[CH3:14][C:15]1[C:24]([S:25]([CH3:28])(=[O:27])=[O:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=[CH:21][C:16]=1[C:17]([O:19]C)=O>C1COCC1>[CH3:14][C:15]1[C:24]([S:25]([CH3:28])(=[O:27])=[O:26])=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=[CH:21][C:16]=1[C:17](=[O:19])[CH2:7][C:6]1[N:2]([CH3:1])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 224591H-1,2,4-Triazole, 1-methyl-HCID 117700237HCID 117700237, compoundHCID 178418339Butyllithium2×

Product 1

HCID 89689483HCID 89689483, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

683 mg (8.22 mmol) of 1-methyl-1,2,4-triazole in 20 ml of THF are admixed under argon at −78° C. with 3.3 ml (8.22 mmol) of butyllithium (2.5M, hexane). After 30 min, 1.22 g (8.63 mmol) of methyl iodide, dissolved in 2 ml of THF, are added, the cooling bath is removed and the mixture is left to reach RT. The mixture is cooled again to −78° C. and admixed with 3.3 ml (8.22 mmol) of butyllithium (2.5M, hexane). After 15 min, 1.22 g (4.12 mmol) of methyl 2-methyl-3-(methylsulfonyl)-4-trifluoromethylbenzoate are added and the mixture is left to thaw overnight. The mixture is quenched with ammonium chloride solution and extracted with EE. The organic phase is washed with NaHCO3 solution and NaCl solution, dried, evaporated and purified by means of RP-HPLC (acetonitrile/water). Yield 255 mg (17%). 1H NMR, CDCl3, 400 MHz: 7.90 (s, 1H), 7.82 (d, 1H), 7.72 (d, 1H), 5.57 (s, 1H), 3.85 (s, 3H), 3.27 (s, 3H), 2.84 (s, 3H).

Workup

  1. additionare added
  2. customthe cooling bath is removed
  3. waitthe mixture is left
  4. customto reach RT
  5. waitAfter 15 min
  6. waitthe mixture is left to thaw overnight
  7. customThe mixture is quenched with ammonium chloride solution
  8. extractionextracted with EE
  9. washThe organic phase is washed with NaHCO3 solution and NaCl solution
  10. customdried
  11. customevaporated
  12. custompurified by means of RP-HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-7928c26078124c0b8780ee9eef286d3a
Source dataset
uspto-grants-2015_08
Patent number
US09107414B2

Reaction notes

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