Triethylamine → (1-(2,6-Dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methyl methanesulfonate

HRID 424780Notes

Reaction equation

HRID 424780 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[N:10]1.CCN(CC)CC.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][S:27]([CH3:26])(=[O:29])=[O:28])=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]=[N:10]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 45790389(1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 86629251(1-(2,6-Dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-yl]-methanol (0.100 g) in dichloromethane (2 mL) is added Et3N (0.25 mL) followed by methanesulfonyl chloride (0.075 mL). The reaction mixture is stirred at room temperature for 2 h. The reaction is diluted with ethyl acetate (20 mL) and washed with water (2×20 mL). The organic layer is dried (Na2SO4) and concentrated under reduced pressure to give the title compound (101 mg). 1H NMR (400 MHz, CDCl3): δ 7.40-7.60 (m, 3H), 5.10 (s, 2H), 3.20-3.30 (m, 1H), 2.85 (s, 3H), and 1.40-1.50 (d, 6H).

Workup

  1. washwashed with water (2×20 mL)
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78ecd16ea69a4d2dbf9942bc376ee49d
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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