Triethylamine → 5-(chloro(3-ethylphenyl)methyl)-1-methyl-3-phenyl-1H-1,2,4-triazole

HRID 2105054Notes

Reaction equation

HRID 2105054 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:9]([C:11]2[N:12]([CH3:22])[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)O)[CH:6]=[CH:7][CH:8]=1)[CH3:2].CCN(CC)CC.CS([Cl:34])(=O)=O>C(Cl)Cl>[Cl:34][CH:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=1)[C:11]1[N:12]([CH3:22])[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57803786(3-ethylphenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

Product 1

HCID 578039035-(chloro(3-ethylphenyl)methyl)-1-methyl-3-phenyl-1H-1,2,4-triazoleYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Intermediate 370.2 (350 mg, 1.2 mmol) was dissolved in CH2Cl2 (10 mL) and Et3N (0.50 mL, 3.6 mmol) and cooled to 0° C., MsCl (0.092 mL, 1.2 mmol) was added dropwise and the mixture was stirred at 0° C. for 2 h. The reaction mixture was diluted with CH2Cl2 (20 mL), washed with H2O, brine, dried (Na2SO4) and concentrated to yield 370 mg of Intermediate 370.3 as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.15 (t, J=7.58 Hz, 3H) 2.56 (q, 2H) 3.71 (s, 3H) 6.30 (s, 1H) 7.09-7.16 (m, 1H) 7.21-7.29 (m, 2H) 7.28-7.43 (m, 3H) 7.99-8.05 (m, 2H).

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1c28c910f52548f4941c87b639ddaa5e
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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