4-Toluenesulfonyl chloride → HCID 18406949, compound

HRID 1016411Notes

Reaction equation

HRID 1016411 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:15])[N:10]=[N:11][C:12]=1[CH2:13][OH:14].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])=[N:10][NH:11][C:12]=1[CH2:13][OH:14]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18406920HCID 18406920, compound

Product 1

HCID 18406949HCID 18406949, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-(2-fluorophenyl)-5-(hydroxymethyl)pyrazol-3-one (28.7 g, 0.138 mol) in dry dichloromethane (300 ml) was added p-toluenesulfonyl chloride (28.9 g, 0.152 mol) followed by triethylamine (21.2 ml, 0.152 mol) dropwise. The solution was stirred at room temperature for 2 days. Dichloromethane (300 ml) was then added to dilute and the solution was washed with brine (300 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography with 0%→40% ethyl acetate/dichloromethane as eluent to give the title compound (23.7 g). Data for the title compound: 1H NMR (360 MHz, DMSO) δ 2.34 (3H, s), 4.66 (2H, s), 6.94 (1H, t), 7.06 (3H, m), 7.17-7.25 (2H, m), 7.51 (2H, d); MS (ES+) m/e 362 [MH]+.

Workup

  1. additionto dilute
  2. washthe solution was washed with brine (300 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography with 0%→40% ethyl acetate/dichloromethane as eluent

Sources & evidence

ORD record
ord-9c3997fa837545b8bc6250d8221ebf25
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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