4-Toluenesulfonyl chloride → HCID 561427, compound

HRID 2094941Notes

Reaction equation

HRID 2094941 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:9])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 163764-nitro-1H-pyrazole

Product 1

HCID 561427HCID 561427, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-nitro-1H-pyrazole (500 mg, 4.4 mmol), 4-methylbenzene-1-sulfonyl chloride (840 mg, 4.4 mmol), and triethylamine (510 mg, 5 mmol) were stirred in DMF (25 mL) at 80° C. for 1 hour. The reaction was cooled, diluted with H2O (200 mL) and extracted with ethyl acetate (3×, 100 ml). The organic phase was washed with aqueous 1N HCl (200 mL) and H2O (200 mL), dried over sodium sulfate, filtered and concentrated on the rotovap. The solid was triturated with hexanes to afford 4-nitro-1-tosyl-1H-pyrazole (600 mg, 50%) as an off white solid. 1H NMR (DMSO-d6, 400 MHz) δ 2.40 (s, 3H), 7.52 (d, 2H, J=8.4 Hz), 7.98 (d, 2H, J=8.8 Hz), 8.57 (s, 1H), 9.58 (s, 1H).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (3×, 100 ml)
  3. washThe organic phase was washed with aqueous 1N HCl (200 mL) and H2O (200 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on the rotovap
  7. customThe solid was triturated with hexanes

Sources & evidence

ORD record
ord-7f4479d470464e4fb02adb9f39a56414
Source dataset
uspto-grants-2013_05
Patent number
US08445692B2

Reaction notes

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