4-Toluenesulfonyl chloride → HCID 11438722, compound

HRID 1016402Notes

Reaction equation

HRID 1016402 reaction equation
[C:1]([C:5]1[C:6](=[O:12])[N:7]=[N:8][C:9]=1[CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[C:1]([C:5]1[C:6]([O:12][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])=[N:7][NH:8][C:9]=1[CH2:10][OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 184068973H-Pyrazol-3-one, 4-(1,1-dimethylethyl)-5-(hydroxymethyl)-

Product 1

HCID 11438722HCID 11438722, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-tert-butyl-5-hydroxymethylpyrazol-3-one (6.25 g, 0.037 mol) in dry dichloromethane (200 ml) was added p-toluene sulfonyl chloride (9.8 g, 0.051 mol) followed by triethylamine (6.14 ml, 0.044 mol) dropwise. The solution was stirred at room temperature for 3 days. Dichloromethane (250 ml) was then added to dilute and the solution was washed with brine (250 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography with 0%→30% ethyl acetate/dichloromethane as eluent to give the title compound (7.5 g). Data for the title compound: 1H NMR (400 MHz, DMSO) δ 1.28 (9H, s), 2.43 (3H, s), 4.49 (2H, m), 5.32 (1H, m), 7.47 (2H, m), 7.86 (2H, m), 12.28 (1H, s); MS (ES+) m/e 325 [MH]+.

Workup

  1. additionto dilute
  2. washthe solution was washed with brine (250 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography with 0%→30% ethyl acetate/dichloromethane as eluent

Sources & evidence

ORD record
ord-59043d2841704686a7a20fde1fc5ecad
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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